Category: piperidines

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

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

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

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

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

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

Mohd Sarofil, Anith Dzhanxinah published the artcileToad egg-like bismuth nanoparticles encapsulated in an N-doped carbon microrod via supercritical acetone as anodes in lithium-ion batteries, Computed Properties of 826-36-8, the publication is Journal of Industrial and Engineering Chemistry (Amsterdam, Netherlands) (2022), 128-141, database is CAplus.

A toad egg-inspired structure comprising bismuth (Bi) nanoparticles (NPs) contained in a carbon microrod shell (Bi@C) was synthesized via the one-pot supercritical acetone (scAct) route and subsequent carbonization. During the formation of Bi NPs in scAct in the presence of nitric acid, a few decomposed acetone mols. acted as carbon sources, which generated an albumen-like N-doped carbon microrod with an average shell thickness of 38 nm and were embedded with yolk-like Bi NPs having size in the range of 30-200 nm. The densely packed Bi NPs inside the carbon micron shell resulted in a high Bi loading of 78 wt%. When utilized for Li storage, the Bi@C delivered a high reversible capacity of 337 mAh g^-1 after 70 cycles at 0.05 A g^-1, long-term cyclability of 0.04 decay per cycle for 1000 cycles at 1 A g^-1, and high volumetric energy d. of 870 mAh cm^-3. The use of a mixed ether- and ester-based electrolyte in the Bi@C cell reduced the resistivity and increased the capacitive contribution, thereby resulting in a better high-rate performance and long-term stability than those obtained using conventional ester-based electrolytes.

Journal of Industrial and Engineering Chemistry (Amsterdam, Netherlands) 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, Computed Properties of 826-36-8.

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

Herbrandson, Harry F. published the artcileDerivatives of aromatic sulfinic acids. II. The reaction of thionyl chloride with sulfinic esters, Safety of 1-(Phenylsulfinyl)piperidine, the publication is Journal of the American Chemical Society (1956), 2576-8, database is CAplus.

cf. C.A. 49, 9370i. PhSOCl (22.5 g.) added to 11.1 g. dry pyridine and 5 g. absolute MeOH in 60 cc. dry Et₂O, the mixture kept at -10° until no more precipitate was formed, and diluted with H₂O, the Et₂O layer washed, dried, and evaporated, and the residue distilled yielded 14.0 g. PhSO₂Me (I), b_0.04 67-8°, b_0.03 63°, n_D²⁰ 1.5400. In the same manner was prepared p-MeC₆H₄SO₂Me (II), 91%, b_0.001 68°, n_D²⁰ 1.5380. II (20.1 g.) and 14.0 g. pure SOCl₂ kept a few days in the dark and distilled gave 3.5 g. ClCO₂Me, b. 104-6°, n_D²⁰ 1.4629, and 18.7 g. p-MeC₆H₄SOCl, lemon-yellow oil, b_0.012 79°, n_D²⁰ 1.6007; it gave with NH₃ in dry Et₂O the p-MeC₆H₄SONH₂, m. 120-20.5° (from aqueous EtOH). I gave in the same manner 84% PhSOCl, yellow oil, b_0.012 65° [PhSONH₂, m. 122° (from aqueous EtOH); piperidide, m. 82-3° (from petr. ether)]. l-Menthyl 1-p-toluenesulfinate (III), m. 106-7° (corrected), [α]_D²⁵ -199.19° (c 2, Me₂CO), was prepared by the method of Phillips (C.A. 20, 397). Et₄NBr in H₂O treated with a slight excess Ag₂O, the mixture triturated twice, and the filtrate acidified to Congo red with 20% HCl and evaporated gave Et₄NCl (IV). A series of kinetic runs was carried out with III and SOCl₂ in PhNO₂ at 24.88 ± 0.05° (molar concentrations of IV, SOCl₂, and IV, and k × 10⁴ sec.^-1 given): 0.0554, 0.0616, 0.00093, 0.62; 0.0551, 0.0616, 0.00-213, 1.18; 0.0626, 0.0616, 0.00309, 1.68; 0.0590, 0.123, 0.00309, 1.92; 0.0516, 0.0616, 0.00425, 2.30; 0.0604, 0.0616, 0.00463, 2.06; 0.0779, 0.0616, 0.00463, 2.12; 0.0520, 0.0616, 0.00850, 3.55; 0.0409, 0.0616, 0.0106, 3.80; 0.0635, 0.0616, 0.0160, 4.28; 0.0548, 0.0492, 0.0213, 3.82; 0.0423, 0.0492, 0.0213, 4.24; 0.0774, 0.123, 0, 0; 0.0542, 0, 0.00617, 0; 0.0845, 0, 0.0213,0; 0.0663, 0, – (0.00525 HCl), 0; 0.0594, 0.0616, – (0.00525 HCl), 0; 0.0510, 0.0616, 0.00378 (MeOH), 0; 0.0408, 0.0616, – (0.0035 H₂O), 0; 0.0732, 0.0860, 0.0232, 7.30; 0.0703, 0.0860, 0.0232 + 0.1M SO₂, 7.63. In the absence of added chloride the reaction is slow; it is 1st order in ester and 1st order in added chloride ion. Trace impurities of the SOCl₂, probably mainly HCl, also affect the rate.

Journal of the American Chemical Society 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 C11H15NOS, Safety of 1-(Phenylsulfinyl)piperidine.

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

Yang, Xianglong published the artcileSuperoxide anion and singlet oxygen dominated faster photocatalytic elimination of nitric oxide over defective bismuth molybdates heterojunctions, Quality Control of 826-36-8, the publication is Journal of Colloid and Interface Science (2022), 248-258, database is CAplus and MEDLINE.

Establishing an ideal photocatalytic system with efficient reactive oxygen species (ROS) generation has been regarded as the linchpin for realizing efficient nitric oxide (NO) removal and unveiling the ROS-mediated mechanism. In this work, a novel oxygen-deficient 0D/1D Bi_3.64Mo_0.36O_6.55/Bi₂MoO₆ heterojunctions (BMO-12-H) were successfully synthesized under the enlightenment of clarified crystal growth mechanism of bismuth molybdates. Because of the synergies between defect-engineering and heterojunction-construction, BMO-12-H demonstrated improved photoelectrochem. properties and O₂ adsorption capacity, which in turn facilitated the ROS generation and conversion. The enhancement of •O_-2 and ¹O₂ endowed BMO-12-H with strengthened NO removal efficiency (59%) with a rate constant of 12.6*10^-2 min^-1. A conceivable NO removal mechanism dominated by •O_-2 and ¹O₂ was proposed and verified based on the theor. calculations and in-situ IR spectroscopy tests, where hazardous NO was oxidized following two different exothermic pathways: the •O_-2-induced NO → NO_-3 process and the ¹O₂-induced NO → NO₂ → NO_-3 process. This work offers a basic guideline for accelerating ROS generation by integrating defect-engineering and heterojunction-construction, and provides new insights into the mechanism of efficient NO removal dominated by •O_-2 and ¹O₂.

Journal of Colloid and Interface Science 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 C10H10CoF6P, Quality Control of 826-36-8.

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

Wang, Xiaolei published the artcileEfficient activation of peroxymonosulfate by copper sulfide for diethyl phthalate degradation: Performance, radical generation and mechanism, HPLC of Formula: 826-36-8, the publication is Science of the Total Environment (2020), 142387, database is CAplus and MEDLINE.

Copper-containing minerals have been extensively used in Fenton-like processes for degradation of pollutants and have exhibited great potential for environmental remediation. This work reports the first use of copper sulfide (CuS), a typical Cu-mineral, for the activation of peroxymonosulfate (PMS) for pollutant degradation; the study also elucidates the underlying mechanism of these processes. Copper sulfide effectively activated PMS to degrade di-Et phthalate (DEP). ESR, free radical quenching, XPS, X-ray diffraction analyses and DFT calculations confirmed that Ξ Cu (I)/ ΞCu (II) cycling on the surface of CuS provided the main pathway to activate PMS to produce highly oxidative species. Unlike conventional sulfate radical-based PMS activation processes, hydroxyl radical (·OH) were found to be the dominant radical in the tested CuS/PMS system, which performed more efficiently than an alternative ·OH-based oxidation system (CuS/H₂O₂) for DEP degradation In addition, the presence of anions such Cl- and NO^-3 has limited inhibition effects on DEP degradation Overall, this study provides an efficient pathway for PMS-based environmental remediation as well as a new insight into the mechanism of PMS activation by Cu-containing minerals.

Science of the Total Environment 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 C6H10O7, HPLC of Formula: 826-36-8.

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