Month: December 2022

Wu, Xuan published the artcileActivation of peroxymonosulfate by magnetic CuFe₂O₄@ZIF-67 composite catalyst for the study on the degradation of methylene blue, Name: 2,2,6,6-Tetramethylpiperidin-4-one, the publication is Colloids and Surfaces, A: Physicochemical and Engineering Aspects (2022), 128278, database is CAplus.

In this research, a novel magnetically recoverable composite catalyst, CuFe₂O₄ @ZIF-67, was synthesized. CuFe₂O₄@ZIF-67 composite catalyst was applied to degrade methylene blue (MB) in water by activating peroxymonosulfate (PMS). The results showed that the degradation rate of MB (20 mg/L) reached 98.9% in 30 min in the 0.2-CuFe₂O₄@ZIF-67 (75 mg/L) + PMS (125 mg/L) system. Both ESR (EPR) studies and radical quenching experiments revealed that SO^–₄•, •OH, ¹O₂ and •O^–₂ were involved in the degradation of MB. We proposed a catalytic mechanism of PMS activation by CuFe₂O₄@ZIF-67. With the synergistic effect of Co³⁺/Co²⁺, Fe³⁺/Fe²⁺ and Cu²⁺/Cu⁺ redox cycles, it can keep its outstanding catalytic activity. Recycling tests showed that the removal rate of MB can still be maintained above 85%, indicating that CuFe₂O₄@ZIF-67 has good reusability. In general, owing to its reusability and excellent catalytic activity, the CuFe₂O₄@ZIF-67 composite catalyst has a good application prospect in water pollution control.

Colloids and Surfaces, A: Physicochemical and Engineering Aspects published new progress about 826-36-8. 826-36-8 belongs to piperidines, auxiliary class Natural product, name is 2,2,6,6-Tetramethylpiperidin-4-one, and the molecular formula is C4H6BrFO2, Name: 2,2,6,6-Tetramethylpiperidin-4-one.

Referemce:
https://en.wikipedia.org/wiki/Piperidine,
Piperidine | C5H11N – PubChem

Cueto-Diaz, Eduardo J. published the artcileCO₂ adsorption capacities of amine-functionalized microporous silica nanoparticles, Formula: C19H21N, the publication is Reactive & Functional Polymers (2022), 105100, database is CAplus.

Efforts on CO₂ capture have intensified as climate change compromises ecosystems and biodiversity. Therefore, it is crucial to develop different methods for CO₂ sequestration to improve solid sorbent capabilities (NPs). To this end, the surface of 200-nm silica nanoparticles (SiO₂NPs) was covalently anchored with aminated ligands, 3-aminopropyltriethoxysilane (APTES), poly(amidoamine) dendrimers (PAMAM) and a short peptide comprising two lysine units, aiming for CO₂ adsorption over a wide range of pressures. Our goal was to explore the influence of functional chem. groups (attached to the SiO₂NPs) on CO₂ sequestration. The observed results showed that at low and high CO₂ gas pressure conditions, typical APTES functionalized SiO₂Np surpassed the CO₂ adsorption capacities of dendritic and peptide-based nanoparticles bearing amine-polymer functionalities, a remarkable effect that was investigated in this work. In addition, a convenient and facile method to decorate and quantify SiO₂ nanoparticles with PAMAM and a short peptide is reported.

Reactive & Functional Polymers published new progress about 35661-58-6. 35661-58-6 belongs to piperidines, auxiliary class Piperidine,Benzene, name is 1-((9H-Fluoren-9-yl)methyl)piperidine, and the molecular formula is C19H21N, Formula: C19H21N.

Referemce:
https://en.wikipedia.org/wiki/Piperidine,
Piperidine | C5H11N – PubChem

Gerleve, Carolin published the artcileTransition-Metal-Free Oxidative Cross-Coupling of Tetraarylborates to Biaryls Using Organic Oxidants, Quality Control of 219543-09-6, the publication is Angewandte Chemie, International Edition (2020), 59(36), 15468-15473, database is CAplus and MEDLINE.

Readily prepared tetraarylborates undergo selective (cross)-coupling through oxidation with Bobbitt’s salt to give sym. and unsym. biaryls. The organic oxoammonium salt can be used either as a stoichiometric oxidant or as a catalyst in combination with in situ generated NO₂ and mol. oxygen as the terminal oxidant. For selected cases, oxidative coupling is also possible with NO₂/O₂ without any addnl. nitroxide-based cocatalyst. Transition-metal-free catalytic oxidative ligand cross-coupling of tetraarylborates is unprecedented and the introduced method provides access to various biaryl and heterobiaryl systems.

Angewandte Chemie, International Edition published new progress about 219543-09-6. 219543-09-6 belongs to piperidines, auxiliary class Piperidine,Fluoride,Salt,Amine,Amide, name is 4-Acetamido-2,2,6,6-tetramethyl-1-oxopiperidinium Tetrafluoroborate, and the molecular formula is C11H21BF4N2O2, Quality Control of 219543-09-6.

Referemce:
https://en.wikipedia.org/wiki/Piperidine,
Piperidine | C5H11N – PubChem

Iniguez, Amanda Balboni published the artcileEWS/FLI Confers Tumor Cell Synthetic Lethality to CDK12 Inhibition in Ewing Sarcoma, Category: piperidines, the publication is Cancer Cell (2018), 33(2), 202-216.e6, database is CAplus and MEDLINE.

Many cancer types are driven by oncogenic transcription factors that have been difficult to drug. Transcriptional inhibitors, however, may offer inroads into targeting these cancers. Through chem. genomics screening, we identified that Ewing sarcoma is a disease with preferential sensitivity to THZ1, a covalent small-mol. CDK7/12/13 inhibitor. The selective CDK12/13 inhibitor, THZ531, impairs DNA damage repair in an EWS/FLI-dependent manner, supporting a synthetic lethal relationship between response to THZ1/THZ531 and EWS/FLI expression. The combination of these mols. with PARP inhibitors showed striking synergy in cell viability and DNA damage assays in vitro and in multiple models of Ewing sarcoma, including a PDX, in vivo without hematopoietic toxicity.

Cancer Cell published new progress about 1702809-17-3. 1702809-17-3 belongs to piperidines, auxiliary class Cell Cycle,CDK, name is (R,E)-N-(4-(3-((5-Chloro-4-(1H-indol-3-yl)pyrimidin-2-yl)amino)piperidine-1-carbonyl)phenyl)-4-(dimethylamino)but-2-enamide, and the molecular formula is C30H32ClN7O2, Category: piperidines.

Referemce:
https://en.wikipedia.org/wiki/Piperidine,
Piperidine | C5H11N – PubChem

Lambert, Kyle M. published the artcileEnhancement of the Oxidizing Power of an Oxoammonium Salt by Electronic Modification of a Distal Group, Name: 4-Acetamido-2,2,6,6-tetramethyl-1-oxopiperidinium Tetrafluoroborate, the publication is Journal of Organic Chemistry (2017), 82(21), 11440-11446, database is CAplus and MEDLINE.

The multigram preparation and characterization of a novel TEMPO-based oxoammonium salt, 2,2,6,6-tetramethyl-4-(2,2,2-trifluoroacetamido)-1-oxopiperidinium tetrafluoroborate (5), and its corresponding nitroxide (4) are reported. The solubility profile of 5 in solvents commonly used for alc. oxidations differs substantially from that of Bobbitt’s salt, 4-acetamido-2,2,6,6-tetramethyl-1-oxopiperidinium tetrafluoroborate (1). The rates of oxidation of a representative series of primary, secondary, and benzylic alcs. by 1 and 5 in acetonitrile solvent at room temperature have been determined, and oxoammonium salt 5 has been found to oxidize alcs. more rapidly than does 1. The rate of oxidation of meta- and para-substituted benzylic alcs. by either 1 or 5 displays a strong linear correlation to Hammett parameters (r > 0.99) with slopes (ρ) of -2.7 and -2.8, resp., indicating that the rate-limiting step in the oxidations involves hydride abstraction from the carbinol carbon of the alc. substrate.

Journal of Organic Chemistry published new progress about 219543-09-6. 219543-09-6 belongs to piperidines, auxiliary class Piperidine,Fluoride,Salt,Amine,Amide, name is 4-Acetamido-2,2,6,6-tetramethyl-1-oxopiperidinium Tetrafluoroborate, and the molecular formula is C11H21BF4N2O2, Name: 4-Acetamido-2,2,6,6-tetramethyl-1-oxopiperidinium Tetrafluoroborate.

Referemce:
https://en.wikipedia.org/wiki/Piperidine,
Piperidine | C5H11N – PubChem

Entooru, Keshamma published the artcileGC-MS analysis of bioactive components and evaluation of in-vitro pancreatic lipase inhibitory activity of aqueous extracts of Pleurotus eryngii, Application In Synthesis of 826-36-8, the publication is International Journal of Chemical Studies (2021), 9(2), 1141-1145, database is CAplus.

Present study was designed to conduct with main purpose to determine bioactive components and evaluation of aqueous extract of Pleurotus eryngii for in-vitro pancreatic lipase inhibitory activity. GC-MS anal. was carried out to determine the bioactive components and in-vitro pancreatic lipase inhibitory assay was carried out to determine IC50 values of aqueous extracts of Pleurotus eryngii. The results of the present study depicted that the aqueous extracts of Pleurotus eryngii possess in-vitro pancreatic lipase inhibitory activities at the concentration of 1-30μg/mL and this could be attributed to the prevailing compounds identified in the GC-MS anal. i.e., conhydrin, di-Et phthalate, phthalic acid-Bu hex-3-yl ester (alkaloids), ar-turmerone (sesquiterpenoid), palmitic acid, myristic acid, phenol and benzoic acid from ethanolic extract of Pleurotus eryngii. In conclusion, polyphenols, alkaloids terpenoids and Vitamin B class of secondary metabolites majorly identified in GC-MS anal. of aqueous extract of Pleurotus eryngii has been reported to possess the in-vitro pancreatic lipase inhibitory activities. Hence, further in-vivo studies in exptl. induced obese animal models could be recommended to access the safety and efficacy of aqueous extracts of Pleurotus eryngii to strongly recommend them as natural antiobesity agents in the formulations of natural antiobesity drugs.

International Journal of Chemical Studies published new progress about 826-36-8. 826-36-8 belongs to piperidines, auxiliary class Natural product, name is 2,2,6,6-Tetramethylpiperidin-4-one, and the molecular formula is C9H17NO, Application In Synthesis of 826-36-8.

Referemce:
https://en.wikipedia.org/wiki/Piperidine,
Piperidine | C5H11N – PubChem

Shyamsunder, Pavithra published the artcileTHZ531 Induces a State of BRCAness in Multiple Myeloma Cells: Synthetic Lethality with Combination Treatment of THZ 531 with DNA Repair Inhibitors, SDS of cas: 1702809-17-3, the publication is International Journal of Molecular Sciences (2022), 23(3), 1207, database is CAplus and MEDLINE.

Multiple myeloma (MM) is a hematol. disease marked by abnormal growth of B cells in bone marrow. Inherent chromosomal instability and DNA damage are major hallmarks of MM, which implicates an aberrant DNA repair mechanism. Studies have implicated a role for CDK12 in the control of expression of DNA damage response genes. In this study, we examined the effect of a small mol. inhibitor of CDK12-THZ531 on MM cells. Treatment of MM cells with THZ531 led to heightened cell death accompanied by an extensive effect on gene expression changes. In particular, we observed downregulation of genes involved in DNA repair pathways. With this insight, we extended our study to identify synthetic lethal mechanisms that could be exploited for the treatment of MM cells. Combination of THZ531 with either DNA-PK inhibitor (KU-0060648) or PARP inhibitor (Olaparib) led to synergistic cell death. In addition, combination treatment of THZ531 with Olaparib significantly reduced tumor burden in animal models. Our findings suggest that using a CDK12 inhibitor in combination with other DNA repair inhibitors may establish an effective therapeutic regimen to benefit myeloma patients.

International Journal of Molecular Sciences published new progress about 1702809-17-3. 1702809-17-3 belongs to piperidines, auxiliary class Cell Cycle,CDK, name is (R,E)-N-(4-(3-((5-Chloro-4-(1H-indol-3-yl)pyrimidin-2-yl)amino)piperidine-1-carbonyl)phenyl)-4-(dimethylamino)but-2-enamide, and the molecular formula is C15H14O3, SDS of cas: 1702809-17-3.

Referemce:
https://en.wikipedia.org/wiki/Piperidine,
Piperidine | C5H11N – PubChem

Biel, John H. published the artcileAntispasmodics. II. Derivatives of N-substituted-3-piperidols, Recommanded Product: 1-Ethylpiperidin-3-ol, the publication is Journal of the American Chemical Society (1955), 2250-6, database is CAplus.

cf. C.A. 48, 694a. The initial finding (loc. cit.) that the replacement of Et₂NCH₂CH₂ by N-ethyl-3-piperidyl in some standard antispasmodic agents yielded compounds of superior spasmolytic activity prompted a more general investigation of the therapeutic usefulness of a variety of 3-piperidyl derivatives Five classes of compounds were synthesized: (1) substituted acetic acid esters of 3-hydroxypiperidine and 3-mercaptopiperidine derivatives; (2) substituted carbamates of N-methyl-3-hydroxypiperidine; (3) N-substituted-3-piperidyl benzhydryl ethers, as well as their thio isosteres; (4) p-aminobenzoates of N-alkyl-3-piperidol; (5) N-methyl-3-piperidyldiphenylmethyl derivatives RCPh₂Y with Y = CONH₂ and CN. The 1st series of compounds yielded a number of potent antispasmodic agents, of which the disubstituted hydroxyacetates appeared to be the most promising ones. The carbamates in series 2 either inhibited or potentiated acetylcholine spasms in the guinea pig ileum depending on the type of substituent. The benzhydryl ethers (series 3) were active spasmolytic agents. Quaternization of the N produced a 10-fold increase in spasmolytic activity. The compounds in series 4 were local anesthetics comparable to procaine in potency. The diphenylacetamide derivatives (5) were moderate antispasmodics. Phenyl-2-thienylglycolic acid was obtained via a mixed benzoin condensation followed by a benzilic acid type rearrangement. The preparation of 3-mercaptopiperidines is described. A general method for obtaining N-aryl-substituted carbamates was developed. BzH (21.2 g.) and 22.4 g. 2-thiophenecarboxaldehyde in 100 cc. absolute EtOH treated with 20 g. KCN in 40 cc. H₂O, the mixture refluxed 1.5 h. with stirring, treated with 250 cc. 50% aqueous EtOH and refrigerated, the orange-yellow precipitate filtered, washed with H₂O, stirred with 10% aqueous NaHCO₃, filtered, suspended in dilute aqueous K₂CO₃, filtered, washed with H₂O, and recrystallized from aqueous EtOH yielded 21.5 g. 2-thienyl α-phenyl-α-hydroxymethyl ketone (I), m. 132-4°. I (10.6 g.), 5.0 g. NH₄NO₃, 0.1 g. Cu(OAc)₂, and 35 cc. 80% aqueous AcOH refluxed 1.5 h. with stirring, cooled, seeded, allowed to crystallize, diluted with H₂O, and filtered, and the filter cake washed with H₂O gave 10.1 g. Ph 2-thienyl diketone (II), m. 59-60°. II (15.0 g.) in 30 cc. 95% EtOH added to 15 g. KOH in 30 cc. H₂O, the mixture refluxed 10 min., the EtOH distilled off, the residual aqueous alk. solution acidified with dilute HCl, and the precipitate washed with H₂O, recrystallized from 100 cc. C₆H₆, and decolorized with 5 g. Darco yielded 7.3 g. phenyl-2-thienylglycolic acid, white crystals, m. 127-9°. N-Methyl-3-hydroxypiperidine (230 g.) and 484 g. Me benzilate in 3.0 l. heptane refluxed with stirring to solution, the refluxing solution treated with 10.0 g. NaOMe in 2.0-g. portions during 8-9 h. while removing 75 cc. MeOH, the mixture concentrated to 0.5 volume and diluted with 2 l. Et₂O, the Et₂O-heptane solution washed, dried, and filtered, the solvent removed in vacuo, the oily residue dissolved in 1300 cc. iso-PrOH, the solution acidified with HCl in Et₂O, and the precipitate filtered gave 555 g. N-methyl-3-piperidyl benzilate HCl salt, m. 221-3°; activity against acetylcholine-induced spasms in the guinea pig ileum 0.6 (atropine 1.0) (the spasmolytic activities will be given in parentheses); free base, b_0.20 198-9°; methobromide, m. 234-6° (0.50). Similarly were prepared the following esters of 1-methyl-3-piperidol (acid, b.p./mm. of base, m.p. of HCl salt, m.p. of methobromide given): Ph₂CHCO₂H, -, – (0.01), -; Ph₂NCO₂H, 190-2°/0.15, 215-16° (0.001), 273-4° (0.001); phenylthienylglycolic acid, -, 227-8° (2.0), -; HOCH₂CHPhCO₂H, 160-8°/0.10, -, [H₂SO₄ salt, m. 75° (decomposition) (0.10)], -. 1-Butyl-3-hydroxypiperidine (8.0 g.) and 6.0 g. Et₃N in 50 cc. C₆H₆ treated with stirring with 11.5 g. Ph₂CHCOCl in 50 cc. C₆H₆ below 70°, the mixture held 2 h. at 70° and filtered, and the filtrate fractionated in vacuo yielded 15.5 g. 1-butyl-3-piperidyl diphenylacetate (III), b_0.10 188-91°; III treated in iso-PrOH with MeBr gave III.MeBr, m. 143-5° (0.006). Similarly was prepared the benzilate analog HCl salt (0.06) and the methobromide, m. 144-6° (0.20). Phenylcyclohexylglycolic acid (31.0 g.), 25.0 g. 1-ethyl-3-chloropiperidine, 70 cc. absolute iso-PrOH refluxed 20 h., the solvent distilled off, the residual oil neutralized with dilute aqueous HCl and extracted with Et₂O, the aqueous phase basified with NaOH and extracted with Et₂O, and the extract dried, and distilled gave 24.0 g. 1-ethyl-3-piperidyl phenylcyclohexylglycolate (IV), b_0.05 166-7°; HCl salt, m. 215-17° (0.20). Similarly were prepared the following esters of 1-ethyl-3-piperidol (acid, b.p./mm., and m.p. HCl salt given): Ph₂CHCO₂H, -, – (0.01) [methobromide (0.07)]; Ph₂CHCSOH, -, – (0.20); phenylcyclohexylacetic acid, -, – (0.06); phenylcyclopentylacetic acid, 154-78°/0.04, 181-3° (0.05); phenylcyclopentylglycolic acid, 201°/0.40, 205-7° (0.75); phenylpropylglycolic acid, 150°/10, 166-7° (0.10); phenylthienylglycolic acid, -, 181-2° (0.30); dicyclohexylacetic acid, 151-61°/0.10, 184-5° (0.01); cyclopentylpropylacetic acid, 118-20°/0.03, 116-18° (0.01). In the same general manner were prepared the following esters: 1-isopropyl-3-piperidyl diphenylacetate, b_0.55 180-4°; HCl salt, m. 134-6° (0.002); 1-(β-phenylisopropyl)-3-piperidyl diphenylacetate HCl salt, m. 161-2° (0.0014); 1-methyl-3-piperidyl acetate methiodide, m. 171-2°. 1-Methyl-3-hydroxypiperidine (V) (23.0 g.) in 150 cc. iso-PrOH treated slowly with stirring with 37.0 g. p-O₂NC₆H₄COCl, the mixture refluxed 3 h. with stirring, cooled, and filtered, and the crude product recrystallized from EtOH gave 32 g. 1-methyl-3-piperidyl p-nitrobenzoate HCl salt (VI), m. 218-19°. VI (15.0 g.) in EtOH hydrogenated over 3.0 g. 10% Pd-C at 60 lb. pressure, and the mixture filtered and evaporated in vacuo yielded 13.0 g. p-aminobenzoate HCl salt of 1-methyl-3-piperidol (VII), m. 126° (slow decomposition). Me₂NCOCl (32.3 g.), 34.5 g. V, and 100 cc. dry pyridine refluxed 3 h., cooled, and poured into 700 cc. ice water, the mixture treated with solid NaOH and extracted with Et₂O, and the extract dried and distilled gave 44 g. N,N-dimethylcarbamate of VII, b_3.0 101-3°; methobromide, m. 205-6° (0.00005); (HCl salt, m. 198-9°); the base treated in Me₂CO with an equivalent amount PhCH₂Cl, the solution kept 3 wk at room temperature, and the precipitate filtered gave 7.0 g. PhCH₂Cl salt, m. 199-201°. NaNH₂ (10.8 g.) in 75 cc. dry PhMe treated with 36.6 g. PhCH₂NHPh in 40 cc. dry PhMe, the mixture refluxed 3 h. with stirring, treated with 19.1 g. ClCO₂Me in 40 cc. PhMe, refluxed 4 h. with stirring, and filtered, and the filtrate fractionated gave 36.5 g. Ph(PhCH₂)NCO₂Me (VIII), b_0.035 132-3°. V (19.2 g.) in 600 cc. heptane treated with 40.2 g. VIII, the mixture refluxed and treated with 1.3 g. NaOMe, the MeOH separated through a Dean-Stark trap, the residual mixture concentrated to 0.5 volume, diluted with 300 cc. Et₂O, and filtered, the filtrate washed, dried, and evaporated, and the residual oil fractionated in vacuo yielded 19.3 g. N-phenyl-N-benzylcarbamate of V, b_0.025 169-71°; methobromide, m. 123-4° (0.006). In a similar manner was prepared dibutylcarbamate of V, b_1.0 111-12°; methiodide, m. 103-4° (0.005). In the usual manner was also prepared 1-ethyl-3-piperidyl p-aminobenzoate-HCl, m. 120° (decomposition). V (11.5 g.) added to 2.3 g. molten Na in 150 cc. hot PhMe, the solution refluxed with stirring, treated with 24.7 g. Ph₂CHCl, refluxed 5 h. with stirring, and filtered, the filtrate extracted with 10% HCl, the acid extract washed with Et₂O, made strongly alk., and extracted with Et₂O, and the extract dried and distilled gave 4.5 g. benzhydryl ether (IX) of V, b_0.11 160-1°; IX.HCl, m. 70° (decomposition) (0.01); IX.MeBr, m. 186-7° (0.10) (from iso-PrOH). Ph₂CHCl (40.4 g.) and 46.0 g. V in 100 cc. PhMe refluxed 24 h. with stirring, the mixture filtered, and the filtrate fractionated gave 37.0 g. IX, b_0.08 140-7°. NaOH (13.5 g.) in 27 cc. H₂O added with stirring to 25.1 g. [Ph₂CHSC(NH₂)₂] Cl and 90 cc. EtOH, the mixture stirred 0.5 h. at 40°, treated with 15.4 g. 1-ethyl-3-chloropiperidine (X), refluxed 2 h. with stirring, cooled, poured into 500 cc. H₂O, and extracted with Et₂O, and the extract dried and distilled gave 23.1 g. 1-ethyl-3-piperidyl thiobenzhydryl ether (XI), oil, which was too heat-labile to be distilled XI in Et₂O-iso-PrOH treated with HCl in Et₂O gave XI.HCl, m. 145-6°; XI.MeBr, m. 158-61° (0.075). X (133 g.) and 69 g. AcSH in 500 cc. absolute iso-PrOH refluxed 15 h., the alc. distilled off, the oily residue treated with 250 cc. H₂O and 400 cc. Et₂O, the mixture treated with 134 g. K₂CO₃ in 200 cc. H₂O, the aqueous phase extracted repeatedly with Et₂O, and the extract dried and distilled gave 87.4 g. 1-ethyl-3-piperidyl thioacetate (XII), b_0.35 66°, n_D²⁰ 1.4963. XII (88.3 g.) added with stirring at room temperature to 1200 cc. 6% aqueous NaOH, the mixture stirred 2 h. at 20°, the solution neutralized with 94 cc. glacial AcOH, saturated with 800 g. (NH₄)₂SO₄, and extracted continuously with Et₂O, and the extract distilled gave 39 g. 1-ethyl-3-mercaptopiperidine (XIII), b_1.7 57.5°, n_D²⁰ 1.4956. XIII (11.7 g.) in 25 cc. treated with stirring and cooling with 14.8 g. p-O₂NC₆H₄COCl in 50 cc. PhMe, the solution refluxed 0.5 h., cooled, and filtered, and the filter residue recrystallized twice from iso-PrOH yielded 19.3 g. 1-ethyl-3-piperidyl p-nitrothiobenzoate-HCl salt, white crystals, m. 149-51°. Ph₂CHCN (116 g.) and 23.4 g. NaNH₂ in 500 cc. dry PhMe refluxed 6 h. with stirring, the hot mixture treated with 160 g. X in 200 cc. dry PhMe, the mixture stirred 20 h. with refluxing, cooled, and extracted with 10% aqueous HCl, the acid extract washed with Et₂O, made alk. with 200 g. KOH in 200 cc. H₂O, and extracted with Et₂O, and the extract dried and fractionated yielded 140 g. 1-methyl-x-(diphenylcyanomethyl)piperidine (XIV), b_0.05 182-6°. XIV (58.0 g.) in 250 cc. EtOH treated with 19.0 g. MeBr, the mixture kept 3 days at room temperature, the precipitate filtered off to yield 40.0 g. product (fraction A), m. 259-61° (decomposition), the filtrate evaporated to dryness, the residue suspended in 200 cc. iso-PrOH, and the insoluble material filtered off yielded 33.0 g. product (fraction B), m. 255-63° (decomposition); the filtrate evaporated to dryness gave 4.5 g. addnl. B; A recrystallized twice from EtOH yielded 30.0 g. XIV.MeBr, m. 263-5° (decomposition); B recrystallized 3 times from iso-PrOH yielded 17.0 g. isomeric XIV.MeBr, m. 278-81° (decomposition); a mixture of A and B melted at 238-42° (decomposition). XIV (50 g.) heated 3 h. on the steam bath with 500 cc. 90% H₂SO₄, the mixture poured onto ice, neutralized with 700 cc. concentrated NH₄OH, and extracted with Et₂O, the white solid separating in the aqueous and the Et₂O phase filtered off to yield 6.4 g. material (fraction C), m. 216-24°, the Et₂O distilled off, the residue suspended twice in 100 cc. boiling Me₂CO and filtered to give 10.3 g. insoluble material (fraction D), m. 227-8°, the combined Me₂CO filtrates evaporated to dryness, and the oily residue crystallized from Et₂O, and the Et₂O suspension filtered gave 5.2 g. material (fraction E), m. 150-3°. C and D combined and recrystallized from 5:1 CHCl₃-heptane yielded 6.0 g., material (fraction F), m. 228-30°. E (3.08 g.) in 25 cc. Me₂CO and 5 cc. iso-PrOH treated with 0.95 g. MeBr yielded 3.90 g. gave 1-methyl-x-diphenylcarboxamidomethylpiperidine (XV).MeBr, m. 259-60° (decomposition). F (2.5 g.) in 25 cc. EtOH gave with 0.70 g. MeBr 1.8 g. isomeric XIV.MeBr, m. 315-16°.

Journal of the American Chemical Society published new progress about 13444-24-1. 13444-24-1 belongs to piperidines, auxiliary class Piperidine,Alcohol, name is 1-Ethylpiperidin-3-ol, and the molecular formula is C7H15NO, Recommanded Product: 1-Ethylpiperidin-3-ol.

Referemce:
https://en.wikipedia.org/wiki/Piperidine,
Piperidine | C5H11N – PubChem

Ma, Yunxi published the artcileThe 9-fluorenylmethyloxycarbonyl group as a 5′-OH protection in oligonucleotide synthesis, Application of 1-((9H-Fluoren-9-yl)methyl)piperidine, the publication is Biopolymers (1989), 28(5), 965-73, database is CAplus and MEDLINE.

Oligo-DNAs are synthesized on a solid support using the 9-fluorenylmethyloxycarbonyl group as a 5′-OH base labile protection. The synthesis of the pure protected nucleotides, a relevant phosphoramidite-type strategy of coupling, and the optimization of the deprotection steps are described.

Biopolymers published new progress about 35661-58-6. 35661-58-6 belongs to piperidines, auxiliary class Piperidine,Benzene, name is 1-((9H-Fluoren-9-yl)methyl)piperidine, and the molecular formula is C19H21N, Application of 1-((9H-Fluoren-9-yl)methyl)piperidine.

Referemce:
https://en.wikipedia.org/wiki/Piperidine,
Piperidine | C5H11N – PubChem

Shapiro, Seymour L. published the artcileAntihypertensive agents. III. Dialkylaminoalkoxypiperidines and related compounds, Computed Properties of 13444-24-1, the publication is Journal of Organic Chemistry (1960), 291-3, database is CAplus.

cf. CA 52, 18396h; 54, 6775c. Reductive alkylation of N-alkyl-3-piperidinols with HCHO and AcH, resp., gave 73% N-methyl-3-piperidinol, b₄₀ 103-4°, and 51% N-ethyl-3-piperidinol, b₄₀ 126-8°. 3-Pyridinemethanol (66.8 g.) in 500 ml. MeCN cooled to -5° during the addition of 95 g. MeBr, and the mixture stored 20 hrs. at 20° gave 89 g. 3-(hydroxymethyl)-1-methylpyridinium bromide, m. 92-4° (iso-PrOH-isopropyl ether). 1-Hydroxymethyl-3-piperidinomethanol-HBr, prepared in 70% yield, m. 113-15° (alc.-MeCOEt). 4-Pyridinemethanol (89.1 g.) and 133 g. EtBr in 800 ml. MeCN refluxed 24 hrs. gave 170 g. crude 4-hydroxymethyl-1-ethylpyridinium bromide (I). Crude I hydrogenated directly and converted into the base with 40% NaOH, and the mixture salted, extracted with Et₂O, and dried gave 31% 4-hydroxymethyl-1-ethylpiperidine. 2-Pyridinemethanol (22 g.) and 40.7 g. PhCH₂CH₂Br in 250 ml. MeCN refluxed 22 hrs. gave 19 g. 2-hydroxymethyl-1-phenethylpyridinium bromide (II), m. 158-9° (alc.). II (14 g.) in 250 ml. alc. and 1.3 g. 5% Rh on C on complete hydrogenation after 3 hrs. gave 10 g. 1-phenethyl-2-piperidinemethanol-HBr, m. 157-8°. NaH (3.1 g.) in 50 ml. PhMe treated during 40 min. with 15.4 g. 1-ethyl-3-piperidinol in 50 ml. PhMe, stirred 2 hrs. at 20°, then refluxed 2 hrs., treated over 1 hr. with 38.4 g. Me₂N(CH₂)₃Cl.HCl in H₂O, made basic, extracted with PhMe, and the mixture refluxed 6 hrs. gave 9.8 g. 3-(3-dimethylaminopropoxy)-1-ethylpiperidine (III). Addition of 3.2 g. III in 10 ml. MeCN to 4.7 g. MeI in 15 ml. MeCN after 20 hrs. gave 4.7 g. 3-(3-dimethylaminopropoxy)-1-ethyl-1-methylpiperidinium iodide-MeI. The following (dialkylaminoalkoxy)alkylpiperidines were thus obtained (1-substituent, 2nd substituent, % yield, m.p. or b.p./mm. given): Me, 3-O-(CH₂)₂NMe₂, 11, 100-3°/9; Me, 3-O(CH₂)₂NMe₂ (di-MeI salt), 60, 294-7°; Et, 3-O(CH₂)₂NMe₂, 17, 102-6°/8; Me, 3-O(CH₂)₃NMe₂, 50, 142-4°/35; Me, 3-O(CH₂)₃-NMe₂ (di-MeI salt), 85, 214-16°; Me, 3-O(CH₂)₃NMe₂, (di-EtI salt), 71, 171-4°; Et, 3-O(CH₂)₃NMe₂, 38, 116-18°/6; Et, 3-O(CH₂)₃NMe₂ (di-MeI salt), 52, 197-200°; Me, 3-CH₂O(CH₂)₂NEt₂, 10, 113°/2; Et, 4-CH₂O(CH₂)₂-NEt₂, 40,106°/0.9; PhCH₂CH₂, 2-CH₂O(CH₂)₂NEt₂, 4, 120-4°/0.08.

Journal of Organic Chemistry published new progress about 13444-24-1. 13444-24-1 belongs to piperidines, auxiliary class Piperidine,Alcohol, name is 1-Ethylpiperidin-3-ol, and the molecular formula is C9H6ClNS, Computed Properties of 13444-24-1.

Referemce:
https://en.wikipedia.org/wiki/Piperidine,
Piperidine | C5H11N – PubChem