Day: November 21, 2022

Thomas, Aleena published the artcileTrichloroacetic acid fueled practical amine purifications, Quality Control of 826-36-8, the publication is Beilstein Journal of Organic Chemistry (2022), 225-231, database is CAplus and MEDLINE.

On out of equilibrium mol. machinery, using trichloroacetic acid (TCA), disclosed a purification technique considerably decreasing the number of operations and the waste generation required for such purifications. At first, TCA triggered the precipitation of the amines through their protonated salt formation, enabling the separation with the impurities. From these amine salts, simple decarboxylation of TCA liberated volatile CO₂ and chloroform afforded directly the pure amines. Through this approach, a broad range of diversely substituted amines were isolated with success.

Beilstein Journal of Organic Chemistry 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 C13H26N2, Quality Control of 826-36-8.

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

Nadaf, AfraQuasar A. published the artcileSynthesis of N-(4-(6-chloro-imidazo[1,2-a]pyridin-2-yl)phenyl) Acetamide Derivatives as Antitubercular Agents, Quality Control of 39546-32-2, the publication is ChemistrySelect (2020), 5(45), 14422-14429, database is CAplus.

The present article reported the synthesis of N-(4-(6-chloroH-imidazo[1,2-a]pyridin-2-yl)phenyl)acetamide derivatives (PINRAc) I [R = piperidin-1-yl, morpholin-4-yl, cyclohexylaminyl, etc.] using 5-chloropyridin-2-amine and 2-bromo-1-(4-nitrophenyl)ethanone in a multi-step protocol. The structures of all the compounds I were characterized by NMR, FT-IR and GCMS. The compounds I were screened for their antitubercular activity against Mycobacterium tuberculosis H37Rv using the microplate Alamar Blue assay. Most of them exhibited good antitubercular activity with MIC in the range of 1.6-25μg/mL and the cytotoxicity study carried out on human embryonic kidney cell line showed no toxicity on the normal cells. The docking study was performed on mycolic acid transporter protein MmpL3 from Mycobacterium smegmatis which supported the in-vitro results.

ChemistrySelect published new progress about 39546-32-2. 39546-32-2 belongs to piperidines, auxiliary class Piperidine,Amine,Amide, name is Piperidine-4-carboxamide, and the molecular formula is C6H12N2O, Quality Control of 39546-32-2.

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

Xing, Hongjie published the artcileUltrasound-assisted synthesized BiFeO₃ as FeOH⁺ promoted peroxymonosulfate activator for highly efficient degradation of tetracycline, Application In Synthesis of 826-36-8, the publication is Journal of Alloys and Compounds (2021), 157281, database is CAplus.

A multiferroic BiFeO3 (BFO) catalyst was fabricated through a mild one-pot hydrothermal process with a bath-ultrasound assisted dissolution of Fe(NO3)3·9H2O for 30 min. X-ray photoemission spectroscopy revealed that the BFO (BFO-u) catalyst with US assisted dissolution of Fe(NO3)3·9H2O in the synthetic process exhibited high Fe2+ and OH- levels, which could be explained to be Fe3+ + H2O → Fe2+ + H+ + •OH. As a result, BFO-u catalyst activated potassium peroxymonosulfate (PMS) efficiently for degrading tetracycline hydrochloride. In particular, visible-light assisted activation of PMS over BFO-u catalyst exhibited the highest degradation rate constant, at 0.352 min-1. Species-trapping experiments revealed that the presence of PMS promoted the generation of •OH, •O-2 and 1O2 that all participated in degrading TCH, in which 1O2 was primarily contributed to the degradation Also, BFO-u catalyst was stable and recyclable and thus suitable for practical applications.

Journal of Alloys and Compounds 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 C13H19Br2ClN2O, Application In Synthesis of 826-36-8.

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

Rzasa, Robert M. published the artcileSynthesis and preliminary biological evaluation of potent and selective 2-(3-alkoxy-1-azetidinyl) quinolines as novel PDE10A inhibitors with improved solubility, Safety of Piperidine-4-carboxamide, the publication is Bioorganic & Medicinal Chemistry (2014), 22(23), 6570-6585, database is CAplus and MEDLINE.

We report the discovery of a novel series of 2-(3-alkoxy-1-azetidinyl) quinolines as potent and selective PDE10A inhibitors. Structure-activity studies improved the solubility (pH 7.4) and maintained high PDE10A activity compared to initial lead compound 3, with select compounds demonstrating good oral bioavailability. X-ray crystallog. studies revealed two distinct binding modes to the catalytic site of the PDE10A enzyme. An ex vivo receptor occupancy assay in rats demonstrated that this series of compounds covered the target within the striatum.

Bioorganic & Medicinal Chemistry published new progress about 39546-32-2. 39546-32-2 belongs to piperidines, auxiliary class Piperidine,Amine,Amide, name is Piperidine-4-carboxamide, and the molecular formula is C6H12N2O, Safety of Piperidine-4-carboxamide.

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

Richter, Heinrich published the artcileMild Metal-Free Tandem α-Alkylation/Cyclization of N-Benzyl Carbamates with Simple Olefins, Computed Properties of 219543-09-6, the publication is Angewandte Chemie, International Edition (2012), 51(34), 8656-8660, S8656/1-S8656/82, database is CAplus and MEDLINE.

Stereoselective synthesis of oxazines was achieved by metal-free tandem α-alkylation/cyclization of N-benzyl carbamates with olefins. E.g., in presence of TEMPO derivative (I) as oxidant, α-alkylation/cyclization of carbamate II (Ad = 1-adamantyl) gave a mixture of separable diastereomers 77% III and 16% IV.

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, Computed Properties of 219543-09-6.

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

Biel, John H. published the artcileAntispasmodics. I. Substituted acetic acid esters of 1-alkyl-3-hydroxypiperidine, Product Details of C7H15NO, the publication is Journal of the American Chemical Society (1952), 1485-8, database is CAplus.

A modification of the method of Paul and Tchelitcheff (C.A. 40, 3757.9) for the preparation of 1-alkyl-3-hydroxypiperidines from furfural (I) or tetrahydrofurfural (II) gave consistently high yields of the alcs. The substituted acetates of the alcs. were potent acetylcholine antagonists. 3-Hydroxypyridine diphenylacetate (III) showed no spasmolytic properties. Tetrahydrofurfuryl chloride (36.0 g.), 68.0 g. Et₂NH, 90.0 g. NaI, and 150 cc. absolute EtOH heated 3 days in a citrate bottle on the steam bath, the mixture filtered, the filtrate evaporated, the residue in water acidified with dilute HCl and extracted with Et₂O, the aqueous phase saturated with KOH, and extracted with Et₂O yielded 25.4 g. N,N-diethyltetrahydrofurfurylamine (IV), b. 64-5°. Reductive aminolysis of I over Raney Ni at 70-90° yielded 71% N-ethyltetrahydrofurfurylamine (V). V (87.0 g.) or 106 g. IV in 54 cc. AcOH at 100-5° treated with 110 g. HBr during 2 h., the mixture neutralized with concentrated KOH below 30°, 350 g. KOH in 300 cc. water added, the mixture distilled, the distillate saturated with KOH and extracted with Et₂O yielded 70 g. N-ethyl-3-hydroxypiperidine (VI), b₁₅ 92-4°; benzoate m. 199-200°. 3-Hydroxypyridine (VII).HCl (39.1 g.) in 250 cc. absolute EtOH hydrogenated at 60 lb. H over 2.2 g. PtO₂ gave 9.0 g. 3-hydroxypiperidine (VIII), m. 61-3°; piperidine-HCl, m. 249-50°. VIII (3.8 g.), 2.3 g. KOH, and 5.9 g. EtI in absolute EtOH refluxed 18 h., cooled, filtered, the filtrate acidified with concentrated HCl, concentrated to dryness in vacuo, the residue dissolved in water and extracted with Et₂O and the aqueous phase saturated with KOH and extracted with Et₂O yielded 4.0 g. VI b₁₅ 93-5°. N-Methyl-3-hydroxypiperidine (IX) prepared in 70% yield from N-methyltetrahydrofurfurylamine b₁₅ 80-2°. VIII (9.0 g.), 13.1 g. 88% HCO₂H, and 8.9 g. 37% HCHO refluxed 24 h. yielded 7.0 g. IX, b₁₅ 81°. PhCH₂CN (117 g.) added during 10 min. to 44.0 g. NaNH₂ in 150 cc. C₆H₆, the mixture refluxed 3 h., 163.0 g. bromocyclohexane in 150 cc. C₆H₆ added at a rate that maintained reflux, the mixture refluxed 8 h., cooled, 250 cc. water added, and the C₆H₆ layer distilled yielded 150 g. α-cyclohexylbenzylnitrile (X), b_0.2 mm. 128-30°, m. 56-8°. Hydrolysis of X yielded 92% phenylcyclohexylacetic acid (XI), m. 153-4°. Ph₂C(OH)CO₂H (22.8 g.) in 150 cc. AcOH at 100° hydrogenated at 60 lb. over PtO₂ yielded 12.7 g. phenylcyclohexylglycolic acid (XII), m. 161-3°. The method of Hoffmann and Schellenberg (C.A. 41, 3074g) yielded 28% phenylcyclopentylglycolic acid (XIII), m. 147-8°. VII (9.5 g.), 23.6 g. Ph₂CHCOCl (XIV), and 50 cc. pyridine refluxed 8 h., the mixture chilled, poured into 600 cc. ice water, the aqueous mixture extracted with Et₂O, the Et₂O evaporated, and the ester distilled in vacuo yielded 26.0 g. III, b_0.5 188-90°; HCl salt (XV), m. 151-2°. XV (26.0 g.) hydrogenated at 60 lb. over 0.5 g. PtO₂, the mixture filtered, the filtrate concentrated in vacuo, the residue in 300 cc. Et₂O refluxed 1 h., filtered, the solid dissolved in water, the solution saturated with KOH, extracted with Et₂O (yielding 3 g. piperidine), the Et₂O filtrate concentrated to dryness, the residue (15 g.) in 200 cc. petr. ether refluxed 1 h., filtered hot [yielding 6.6 g. Ph₂CHCO₂H (XVI), m. 146-8°], and the filtrate cooled yielded 6.0 g. Ph₂CHCO₂Et (XVII), m. 60-60.5°. XVI with LiAlH₄ yielded 77% Ph₂CHCH₂OH, m. 58-9°. XIV and excess NaOEt in absolute EtOH heated a few min. and poured into ice water yielded 80% XVII, m. 59-60°. III (5.0 g.) and 15.0 g. MeI in Et₂O let stand 2 wk in the dark yielded 2.1 g. methiodide, m. 126-8°. N-Alkyl-3-piperidyl esters. Procedure A: XIV (46.0 g.), 25.8 g. VI, and 100 cc. pyridine refluxed 4 h., poured into 800 cc. ice water, the aqueous phase extracted with Et₂O and the extracts evaporated yielded 52.0 g. N-ethyl-3-piperidyl diphenylacetate-HCl. Procedure B: Ph₂C(OH)CO₂H (47.0 g.), 30.5 g. N-ethyl-3-chloropiperidine, and 130 cc. iso-PrOH refluxed 72 h., the solvent removed in vacuo, the residue poured into 200 cc. ice water, acidified with concentrated HCl, extracted with Et₂O, the aqueous layer made alk. with 12 g. NaOH and extracted with Et₂O yielded 49.0 g. N-ethyl-3-piperidyl benzilate-HCl (XVIII), m. 189-90°. Procedure C: The Et ester of XII (21.0 g.), 17.0 g. IX, 0.3 g. Na, and 100 cc. xylene heated at 165° in an oil bath (water and xylene slowly distilled) during 16 h., water, IX, and xylene removed in vacuo, the residue in water acidified with HCl, the aqueous layer extracted with Et₂O, made alk. with KOH, and extracted with Et₂O yielded 3.6 g. N-methyl-3-piperidyl 1-phenylcyclohexylcarboxylate HCl salt, m. 215-16°. XVIII (3.76 g.), and 16.0 g. KOH in alc. refluxed 24 h. yielded 1.2 g. VI, b₁₂ 86-8°; benzoate-HCl, m. 198-9°. Other RCO₂R’ (R’ = 1-ethyl-3-piperidyl) prepared are (R, b.p./mm., salt, and its m.p. given): Ph₂CH, 191-2°/0.18, HCl, 195-6° (MeBr salt, m. 168-9°); Ph(C₆H₁₁)CH, 172-4°/0.55, HCl, 214-16° (MeBr salt, m. 126-7°); Ph₂COH, 207-8°/0.50, HCl, 187-8° (MeBr salt, m. 179-80°); Ph(C₆H₁₁)COH, 166-7°/0.5, HCl, 215-17°; 9-fluorene, -, HCl 226-7°;9-xanthene, -, HCl, 226-7°. Ph₂CHCO₂R (R = 1-methyl-3-piperidyl) b_0.16 173-5° (HCl salt, m. 193-4°).

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, Product Details of C7H15NO.

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

Steiner, Gerd published the artcileTricyclic epines. Novel (E)- and (Z)-11H-dibenz[b,e]azepines as potential central nervous system agents. Variation of the basic side chain, Name: (1-Methylpiperidin-3-yl)methanamine, the publication is Journal of Medicinal Chemistry (1986), 29(10), 1877-88, database is CAplus and MEDLINE.

Dibenzazepinylideneacetonitriles I (R = alkylamino, aminoalkoxy; R¹ = H, Me, Cl; R² = H, Cl) were prepared and their pharmacol. activities were determined The introduction of the cyanomethylene group into the 11-position of the 11H-dibenz[b,e]azepine framework was carried out by a Wittig-Horner reaction under mild conditions. The (E),(Z) isomers were separated by fractional crystallization, assignment being achieved by X-ray anal. I (R = 4-methyl-1-piperazinyl, R¹ = R² = H; R¹ = 3-Me 3-Cl, R² = H; R¹ = H, R² = 8-Cl) show neuroleptic activity 2-7 times that of clozapine. The screening included tests for sedative and anticholinergic activity in mice, apomorphine and tryptamine antagonism in rats, and muscle-relaxing activity in rabbits. The divergence in the activity profile in the case of the separated (E),(Z) isomers has been observed as an interesting new aspect: the (Z) isomers show a significantly higher sedative and muscle-relaxant activity, whereas the (E) isomers possess a higher anticholinergic efficacy and somewhat greater apomorphine antagonism. Broad changes in the basic side chain were made in order to investigate structure-activity relationships. The important geometrical parameters for the mols., obtained by X-ray anal., were compared with the corresponding features in dopamine agonists and antagonists.

Journal of Medicinal Chemistry published new progress about 14613-37-7. 14613-37-7 belongs to piperidines, auxiliary class Piperidine,Amine, name is (1-Methylpiperidin-3-yl)methanamine, and the molecular formula is C25H23NO4, Name: (1-Methylpiperidin-3-yl)methanamine.

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

Tresse, Cedric published the artcileTotal synthesis of tiacumicin B: study of the challenging β-selective glycosylations, Recommanded Product: 1-(Phenylsulfinyl)piperidine, the publication is Chemistry – A European Journal (2021), 27(16), 5230-5239, database is CAplus and MEDLINE.

We give a full account of the total synthesis of tiacumicin B (Tcn-B), a natural glycosylated macrolide with remarkable antibiotic properties. Our strategy is based on our experience with the synthesis of the tiacumicin B aglycon and on unique 1,2-cis-glycosylation steps. We used sulfoxide anomeric leaving-groups in combination with a remote 3-O-picoloyl group on the donors that allowed highly β-selective rhamnosylation and noviosylation that rely on H-bond-mediated aglycon delivery. The rhamnosylated C1-C3 fragment was anchored to the C4-C19 aglycon fragment by a Suzuki-Miyaura cross-coupling. Ring-size-selective Shiina macrolactonization provided a semi-glycosylated aglycon that was engaged directly in the noviolysation step with a virtually total β-selectivity. Finally, a novel deprotection method was devised for the removal of a 2-naphthylmethyl ether on a phenol, and efficient removal of all the protecting groups provided synthetic tiacumicin B.

Chemistry – A European Journal published new progress about 4972-31-0. 4972-31-0 belongs to piperidines, auxiliary class Piperidine,Benzene, name is 1-(Phenylsulfinyl)piperidine, and the molecular formula is C12H16O3, Recommanded Product: 1-(Phenylsulfinyl)piperidine.

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

Bevan, Thomas W. published the artcileA colorful azulene-based protecting group for carboxylic acids, SDS of cas: 35661-58-6, the publication is Tetrahedron (2018), 74(24), 2942-2955, database is CAplus.

An intensely blue-colored protecting group for carboxylic acids has been developed. The protecting group is introduced through Steglich esterification that couples 6-(2-hydroxyethyl)azulene (AzulE) and the carboxylic acid substrate RC(O)OH (R = cyclohexyl, (E,E)-CH₃CH=CH-CH=CH, ([(9H-fluoren-9-ylmethoxy)carbonyl]amino)methyl, etc.). Deprotection is effected under basic conditions by the addition of the amidine base DBU, whereupon cleavage occurs, accompanied by a color change. A two-step deprotection methodol. comprising activation with oxalyl chloride and deprotection with a very mild base was developed for use with base-sensitive substrates. The AzulE esters I were found to be compatible with other commonly employed protecting groups – silyl ethers, MOM acetals – by studying their orthogonal and concomitant deprotections. The stability of the new protecting group towards various synthetic processes – oxidation, reduction, cross-coupling, olefination and treatment with base – provided the basis of a versatility profile. This indicated that AzulE esters are sensitive to strongly oxidizing and basic agents while being compatible with reducing conditions and selected other reactions. The convenience of a highly colored protecting group for tracking material (and avoiding loss of compound) through laboratory processes warrants further investigation of this and/or related species.

Tetrahedron 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, SDS of cas: 35661-58-6.

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

Mathison, Ian W. published the artcileNew compounds. N,N-dimethyl-[3-(1-alkylpiperidy)]carbamates, potential cholinesterase inhibitors, COA of Formula: C7H15NO, the publication is Journal of Pharmaceutical Sciences (1973), 62(1), 158-60, database is CAplus and MEDLINE.

Ten 1-alkylpiperidinyl carbamates [I, R = Me, Et, Me(CH2), n = 2-8] were prepared by condensation of 1-alkyl-3-hydroxypiperidines with Me2NCOCl or by treatment of the hydroxy compound with Cl2CO followed by Me2NH.

Journal of Pharmaceutical Sciences 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, COA of Formula: C7H15NO.

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