Heterocyclic Building Blocks-piperidine

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.914988-10-6,tert-Butyl 3-cyano-4-oxopiperidine-1-carboxylate,as a common compound, the synthetic route is as follows.

914988-10-6, To a stirred solution of sodium bis(trimethylsilyl)amide (1.0M in tetrahydrofuran) (5.89 mL, 5.89 mmol) in tetrahydrofuran (4 mL) at -78C was added slowly tert-butyl 3-cyano-4-oxopiperidine- 1 -carboxylate (1.2 g, 5.35 mmol) in tetrahydrofuran (3 mL). The reaction mixture was stirred for 30 minutes and then treated over 15 minutes with a solution of 1 , 1 , 1 -trifluoro-N-phenyl-N- ((trifluoromethyl)sulfonyl)methanesulfonamide (2.103 g, 5.89 mmol) in tetrahydrofuran (5 mL). The mixture was stirred at -78C for 1.5 hours, allowed to warm to room temperature for 30 minutes and quenched by the addition of water (12.5 mL). The mixture was extracted with ether, and the organic layer was washed with brine, dried over Na2S04, filtered and concentrated in vacuo. The residue was purified by falsh chromatography on Analogix IntelliFlash280 eluting with 5 – 50% ethyl acetate/hexanes to afford the title compound (-85% pure). MS (ESI+) m/z 374 (M+NH4)+.

The synthetic route of 914988-10-6 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; ABBVIE INC.; ABBVIE PHARMACEUTICAL TRADING (SHANGHAI) CO., LTD.; TONG, Yunsong; BRUNCKO, Milan; CLARK, Richard F.; CURTIN, Michael L.; FLORJANCIC, Alan S.; FREY, Robin R.; GONG, Jianchun; HANSEN, Todd M.; JI, Zhiqin; LAI, Chunqiu; MASTRACCHIO, Anthony; MICHAELIDES, Michael; MIYASHIRO, Juliem; RISI, Roberto M.; SONG, Xiaohong; TAO, Zhi-fu; WOODS, Keith W.; ZHU, Guidong; PENNING, Thomas; SOUERS, Andrew; GOSWAMI, Rajeev; IQUTURI, Omprakash Reddy; DABBEERU, Madhu Babu; WO2014/139328; (2014); A1;,
Piperidine – Wikipedia
Piperidine | C5H11N – PubChem

25137-01-3, (R)-Ethyl piperidine-3-carboxylate is a piperidines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Referential Example 3 (3S)-3-aminomethyl-1-(tert-butoxycarbonyl)piperidine The title compound was prepared by a method similar to Referential Example 1, using ethyl (3R)-3-piperidinecarboxylate L(+)-tartarate which was synthesiszed following the method of P. Magnus, et al. [J. Org. Chem., Vol. 56, pp. 1166-1170 (1991)].

25137-01-3, As the paragraph descriping shows that 25137-01-3 is playing an increasingly important role.

Reference：
Patent; BANYU PHARMACEUTICAL CO., LTD.; EP1213281; (2002); A1;,
Piperidine – Wikipedia
Piperidine | C5H11N – PubChem

125224-43-3, ((3S,4R)-4-(4-Fluorophenyl)piperidin-3-yl)methanol is a piperidines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a stirred solution of ((3S, 4R)-4-(4-fluorophenyl)piperidin-3-yl)methanol (1.00 g, 4.8 mmol) in methylene chloride (20 mL), was added triethylamine (1.30 mL, 9.3 mmol) and di-tert-butyl dicarbonate (1.50 g, 6.9 mmol). The resulting reaction mixture was stirred at ambient temperature for 20 h and concentrated in vacuo. The residue was dissolved in ethyl acetate (200 mL) and washed with saturated sodium bicarbonate solution (50 mL) and brine (50 mL); dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated in vacuo, and the residue was purified by column chromatography (30% ethyl acetate in hexanes) to afford (3S,4/?)-te/f-butyl 4- (4-fluorophenyl)-3-(hydroxymethyl)piperidine-1-carboxylate in 92% yield (1.36 g) as a colorless solid: 1H NMR (300 MHz, CDCI3) 7.22 (d, J = 8.4 Hz, 2H), 7.08 (d, J = 8.4 Hz, 2H), 4.50-4.15 (m, 2H), 3.43 (s, 3H), 2.95-2.58 (m, 4H), 1.80-1.49 (m, 2H), 1.49 (s, 9H)., 125224-43-3

The synthetic route of 125224-43-3 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; XENON PHARMACEUTICALS INC.; SUN, Shaoyi; ZENOVA, Alla, Yurevna; CHAFEEV, Mikhail; JIA, Qi; ZHANG, Zaihui; OBALLA, Renata, Marcella; WO2013/64983; (2013); A1;,
Piperidine – Wikipedia
Piperidine | C5H11N – PubChem

220394-97-8, 1-Boc-4-(Cbz-amino)piperidine is a piperidines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

A mixture of tert-butyl 4-{[(benzyloxy)carbonyl]amino}piperidine-1-carboxylate obtained in Example 1a (13.1 g, 39.2 mmol), a 5 N aqueous hydrochloric acid solution (40 ml, 200 mmol) and methanol (40 ml) was stirred at mom temperature for 23 hours. A 5 N aqueous sodium hydroxide solution (40 ml) was added to the reaction mixture under ice-cooling. Water and the solvent were distilled off from the reaction mixture while the mixture was azeotropically distilled with ethanol. Ethanol was added to the residue, the insoluble matter was removed by filtration, and the filtrate was concentrated to give the title compound (9.10 g, yield 99.1%). 1H-NMR (400 MHz, CDCl3) delta ppm; 1.31-1.42 (2H, m), 1.92-2.04 (2H, br), 2.70 (2H, d, J=12 Hz), 3.10 (2H, d, J=12 Hz), 3.56-3.68 (1H, br), 4.72-4.81 (1H, br), 5.09 (2H, s), 7.26-7.40 (5H, m)., 220394-97-8

220394-97-8 1-Boc-4-(Cbz-amino)piperidine 1514305, apiperidines compound, is more and more widely used in various fields.

Reference：
Patent; EISAI R&D MANAGEMENT CO., LTD.; YOSHIDA, Ichiro; OKABE, Tadashi; MATSUMOTO, Yasunobu; WATANABE, Nobuhisa; ONIZAWA, Yuji; OHASHI, Yoshiaki; HARADA, Hitoshi; US2013/65925; (2013); A1;,
Piperidine – Wikipedia
Piperidine | C5H11N – PubChem

495414-81-8, 1-tert-Butyl 4-ethyl 4-(cyanomethyl)piperidine-1,4-dicarboxylate is a piperidines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a mixture of compound c (2.54 g, 8.6 mmol), cobalt chloride hexahydrate (1.02 g, 4.3 mmol) and methanol (50 mL) was added sodium borohydride (1.63 g, 43.1 mmol) under ice-cooling, and the mixture was stirred under ice-cooling for 2 h, and then at room temperature for 2 days, and then 60C for 2 h. Aqueous ammonia (28%, 5 mL) was added thereto, the precipitate was removed by filtration, and the filtration was extract with ethyl acetate(3×40 mL). The organic layer was dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography eluting with ethyl acetate to obtain the desired product d (0.83 g) as a white powder, yield: 39.3%, mp: 153.2-154.4C. 1H NMR (600 MHz, DMSO) delta 7.56 (s, 1H, CONH), 3.81 (d, J = 12.0 Hz, 2H, diazaspiro-CH2), 3.17 (t, J = 6.8 Hz, 2H, diazaspiro-CH2), 2.90 (s, 2H, diazaspiro-CH2), 1.95 (t, J = 6.8 Hz, 2H, diazaspiro-CH2), 1.54-1.48 (m, 2H, diazaspiro-CH2), 1.40 (s, 9H, C(CH3)3), 1.31 (d, J = 13.2 Hz, 2H, diazaspiro-CH2). 13C NMR (151 MHz, DMSO) delta 181.62, 154.68, 79.48, 41.97, 40.58, 38.72, 32.00, 31.82, 28.43. HRMS(ESI): calcd for C13H22N2O3 [M+Na]+, 277.1523, found, 277.1523.

495414-81-8, As the paragraph descriping shows that 495414-81-8 is playing an increasingly important role.

Reference：
Article; Li, Bing; Wang, Kaiyuan; Zhang, Rui; Li, Baihui; Shen, Yangli; Ji, Qinggang; European Journal of Medicinal Chemistry; vol. 182; (2019);,
Piperidine – Wikipedia
Piperidine | C5H11N – PubChem

768-66-1, 2,2,6,6-Tetramethylpiperidine is a piperidines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

768-66-1, 2,2,6,6-tetramethylpiperidine (7.20 kg, 51.1 mol, 3.0 eq., KF=0.30%) was added into a 100 L reactor equipped with a temperature probe and overhead stirrer and mixed at RT under nitrogen protection. THF (50 L) was added into the reactor and stirred. The vessel was purged with nitrogen three times and cooled to 0 C. n-BuLi (20.4 L, 3.0 eq.; 2.5 M hexane solution) was added to the mixture dropwise while keeping the temperature at about 0 C to about 5 C for over one hour. The color of the solution turned yellow. The mixture was stirred at about 0 C to about 5 C for 30 minutes. The mixture was cooled to about -78 C to about -70 C to form Solution A.

As the paragraph descriping shows that 768-66-1 is playing an increasingly important role.

Reference：
Patent; HELSINN THERAPEUTICS (US) INC; HELSINN HEALTHCARE SA; HELSINN ADVANCED SYNTHESIS SA; RUBIO, Silvina Garcia; PERSEGHINI, Mauro; GUAINAZZI, Angelo; PIETRA, Claudio; GIULIANO, Claudio; (110 pag.)WO2019/118298; (2019); A1;,
Piperidine – Wikipedia
Piperidine | C5H11N – PubChem

3518-83-0, N-Ethyl-4-hydroxypiperidine is a piperidines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Example 2 6-Methoxy-2-(4-Methoxyphenyl)-3-(4-[1-Ethylpiperidin-4-oxy]benzoyl)benzo[b]thiophene 6-Methoxy-2-(4-methoxyphenyl)-3-(4-hydroxybenzoyl)benzo[b]thiophene (1.17 g, 3.00 mmol), 4-hydroxy-1-ethylpiperidine (775 mg, 6.00 mmol), triphenylphosphine (1.57 g, 6.00 mmol), and DEAD (6.00 mmol) were converted to product by the procedure of Example 1 to give 827 mg of the title compound. Yield: 55%. MS(FD) 501(M+). EA calculated for C30H31NO4S: C, 71.83; H, 6.23; N, 2.79. Found: C, 71.61; H, 5.94; N, 2.69.

3518-83-0, As the paragraph descriping shows that 3518-83-0 is playing an increasingly important role.

Reference：
Patent; ELI LILLY AND COMPANY; EP905132; (1999); A1;,
Piperidine – Wikipedia
Piperidine | C5H11N – PubChem

683233-14-9, (R)-tert-Butyl 2-(aminomethyl)piperidine-1-carboxylate is a piperidines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a solution of(1S,3?R,6?R,7?R,8?E,11?S,12?R)-6-chloro-7?-methoxy- 11?, 1 2?-dimethyl-l 5? -oxo-3,4-dihydro-2H-spiro [naphthalene- 1,22? – [20joxa[13jthia[1,14jdiazatetracyclo[14.7.2.03,6.019,24jpentacosa[8,16,18,2 4jtetraenej-7?-carbaldehyde 13?,13?-dioxide (44 mg, 0.069 mmol) in 1,2-dichloroethane (1 mL) was added (R)-tert-butyl 2-(aminomethyl)piperidine-1- carboxylate (147 mg, 0.686 mmol). The resulting mixture was then stirred at room temperature for 1 h. Then, sodium triacetoxyborohydride (73 mg, 0.343 mmol) was added in portions. After addition, the mixture was then stirred at room temperature for 3 d. The mixture was purified by silica gel columnchromatography (0% to 20% MeOH/DCM) to provide 2-methyl-2-propanyl (2R)-2-(((((1S,3?R,6?R,7?R,8?E,1 1?S,12?R)-6-chloro-7?-methoxy-11?,12?-dimethyl-13?, 13? -dioxido- 15 ?-oxo-3,4-dihydro-2H-spiro[naphthalene- 1,22? -[20joxa[13jthia[1,14jdiazatetracyclo[14.7.2.03,6.019,24jpentacosa[8,16,18,24jtetraenj -7? -yl)methyl)amino)methyl)- 1 -piperidinecarboxylate (57.6 mg, 0.069mmol, 100 % yield) as a light yellow solid, which was used in the next step. MS (ESI, +ve ion) m/z 839.4 (M+H).

683233-14-9, As the paragraph descriping shows that 683233-14-9 is playing an increasingly important role.

Reference：
Patent; AMGEN INC.; HARRINGTON, Paul E.; ASHTON, Kate; BROWN, Sean P.; KALLER, Matthew R.; KOHN, Todd J.; LANMAN, Brian Alan; LI, Kexue; LI, Yunxiao; LOW, Jonathan D.; MINATTI, Ana Elena; PICKRELL, Alexander J.; STEC, Markian M.; TAYGERLY, Joshua; (991 pag.)WO2018/183418; (2018); A1;,
Piperidine – Wikipedia
Piperidine | C5H11N – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.89895-06-7,1-(Piperidin-4-yl)ethanone hydrochloride,as a common compound, the synthetic route is as follows.

89895-06-7, EXAMPLE 65 5-chloro-2-(piperidin-4-yl)-1H-indole A mixture of 0.60 gm (3.4 mMol) 4-chlorophenylhydrazine hydrochloride and 0.54 mL (6.7 mMol) pyridine in 20 mL ethanol were stirred at 60 C. for 15 minutes. To this mixture was then added 4-acetylpiperidine hydrochloride and the reaction mixture was stirred for 2 hours at 70 C. The reaction mixture was concentrated under reduced pressure and the residue was treated with polyphosphoric acid. This mixture was heated at 90-100 C. for 48 hours. The reaction mixture was quenched with a slurry of ice in 5N sodium hydroxide. The aqueous mixture was extracted well with ethyl acetate. The organic phases were combined, washed with saturated aqueous sodium chloride, dried over sodium sulfate and concentrated under reduced pressure. The residue was subjected to silica gel chromatography, eluding with a dichloromethane gradient containing 4-20% methanol. Fractions containing product were combined and concentrated under reduced pressure to provide 0.26 gm (36%) of the title compound as a tan solid. MS(FD): m/e=234 (M+) EA: Calculated for: C13 H15 N2 Cl: Theory: C, 66.52; H, 6.44; N, 11.93. Found: C, 66.24; H, 6.34; N, 11.73.

The synthetic route of 89895-06-7 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; Eli Lilly and Company; US5846982; (1998); A;,
Piperidine – Wikipedia
Piperidine | C5H11N – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.35856-62-3,Piperidine-1-sulfonyl chloride,as a common compound, the synthetic route is as follows.

To 0.350g (1. 62mmol) of 10001a in 1 OmL CH2CI2 was added 0.23 mL (1. 62mmol) of Et3N, then 0.446g (2. 42mmol) of 10004b in 5 mL CH2CI2 drop wise at rt. The reaction mixture was stirred at rt overnight. The reaction mixture was diluted with EtOAc, washed with a solution of aq. NH4CI and brine. The organic layers was dried over MgS04, filtered, concentrated in vacuo and purified by silica gel chromatography with 6 24% EtOAc in Hexane to yield 0.353g of product. Yield 60%.

35856-62-3, As the paragraph descriping shows that 35856-62-3 is playing an increasingly important role.

Reference：
Patent; SCHERING CORPORATION; WO2005/87721; (2005); A2;,
Piperidine – Wikipedia
Piperidine | C5H11N – PubChem