Category: piperidines

914988-10-6,914988-10-6, tert-Butyl 3-cyano-4-oxopiperidine-1-carboxylate is a piperidines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a solution of tert-butyl 3-cyano-4-oxopiperidine-1-carboxylate (13.6 g, 61 mmol) in 50 mL of dry toluene was added 2-(4-phenoxyphenylamino)acetonitrile (11.38 g, 51 mmol), followed by 4-methylbenzenesulfonic acid (1.36 g, 6.1 mmol). The resulting mixture was heated to reflux with a Dean-Stark for 5 h. After cooling down to RT, the mixture was washed with 50 mL of sat. NaHCO3 solution. The organic phase was collected, the aqueous phase was further extracted with EA (30 mL×3). The combined organic phases were dried over Na2SO4, filtered and concentrated under reduced pressure. The crude residue was purified by chromatograph on 300 g of silica gel (eluting with EA/PE=from to ) to give 7.3 g (27.8%) of the desired compound as a gray solid. 1H NMR (400 MHz, DMSO-d6) delta 7.41-7.34 (m, 2H), 7.28-7.23 (m, 2H), 7.16-7.10 (m, 1H), 7.10-7.05 (m, 2H), 7.04-6.99 (m, 2H), 4.86 (s, 2H), 3.97 (s, 2H), 3.50 (t, J=5.6 Hz, 2H), 2.44 (t, J=5.6 Hz, 2H), 1.42 (s, 9H). MS (ESI) m/e [M+23]+ 430.9

914988-10-6 tert-Butyl 3-cyano-4-oxopiperidine-1-carboxylate 42609283, apiperidines compound, is more and more widely used in various fields.

Reference：
Patent; Wang, Zhiwei; Guo, Yunhang; US2015/5277; (2015); A1;,
Piperidine – Wikipedia
Piperidine | C5H11N – PubChem

1019351-46-2, Methyl 4-aminopiperidine-1-carboxylate is a piperidines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,1019351-46-2

Example VI-4 : 4- [4-(3-FIuoro-phenyl)-6-((3/?)-hydroxymethyl-3,4-dihy dro- ljff-isoquinolm-l-y^-Jl^jSltriazin-l-ylaminol-piperidine-l-carboxylic acid methyl esterStep 1) 4-[4-Chloro-6-(3-fluoro-phenyl)-[ 1 ,3 ,5]triazin-2-ylamino]-piperidine- 1 – carboxylic acid methyl ester DIPEA (583 mg, 1.1 eq) and 4-amino-piperidine-l -carboxylic acid methyl ester (713 mg, 1.1 eq) were sequentially added to 2,4-Dichloro-6-(3- fluoro-phenyl)-[l,3,5]triazine (1.Og) dissolved in CH3CN (20 ml), and stirred for 3 hours. The resulting mixture was diluted with ethyl acetate, and washed successively with water and saturated NaCl. The resulting organic layer was dried over anhydrous magnesium sulfate, and concentrated under a reduced pressure. The resulting residue was purified by column chromatography to obtain the title compound (657 mg).1H NMR (300 MHz, CDCl3) delta 8.22-8.03 (m, 2H), 7.50-7.22 (m, 2H), 5.63-5.58 (m, IH), 4.60-4.10 (m, 3H), 3.72 (s, 3H), 3.12-2.98 (m, 2H), 2.15- 2.04(m, 2H), 1.53-1.40 (m, 2H).

The synthetic route of 1019351-46-2 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; AMOREPACIFIC CORPORATION; CRYSTALGENOMICS, INC.; INDUSTRY-ACADEMIC COOPERATION FOUNDATION, YONSEI UNIVERSITY of Yonsei University; WO2008/72850; (2008); A1;,
Piperidine – Wikipedia
Piperidine | C5H11N – PubChem

936130-82-4, Methyl 4-(piperidin-4-yl)benzoate hydrochloride is a piperidines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

A mixture of X (100 mg, 0.332 mmol), 124-0 (115 mg, 0.450 mmol), and Et3N (75 mu,, 0.54 mmol) in MeOH (5.0 mL) is stirred at ambient temperature for 15 min. The mixture is treated with NaCNBH3 (35.0 mg, 0.550 mmol) and acetic acid (2 drops), and stirred for 16 h. The reaction mixture was concentrated and the resultant residue is purified by flash chromatography (0-10% NH3 in MeOH in DCM) to give 124-1., 936130-82-4

As the paragraph descriping shows that 936130-82-4 is playing an increasingly important role.

Reference：
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; ABEYWARDANE, Asitha; BRUNETTE, Steven Richard; BURKE, Michael Jason; KIRRANE, Thomas Martin, Jr.; MAN, Chuk Chui; MARSHALL, Daniel Richard; PADYANA, Anil Kumar; RAZAVI, Hossein; SIBLEY, Robert; SMITH KEENAN, Lana Louise; SNOW, Roger John; SORCEK, Ronald John; TAKAHASHI, Hidenori; TAYLOR, Steven John; TURNER, Michael Robert; YOUNG, Erick Richard Roush; ZHANG, Qiang; ZHANG, Yunlong; ZINDELL, Renee M.; WO2014/14874; (2014); A1;,
Piperidine – Wikipedia
Piperidine | C5H11N – PubChem

297172-16-8, (4-Methylpiperidin-4-yl)methanol is a piperidines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Diisopropylamine (3.14 inL; 22.23 mmol; 1.1 eq.) was dissolved in THF (60 mL) and cooled to -78 C. Butyl lithium (2.5 M in hexane; 8.89 mL; 22.23 mmol; 1.1 eq.) was then added and the solution was stirred for 30 minutes at -78 C. Ethyl l-benzylpiperidine-4-carboxylate (5 g; 20.21 mmol; 1 eq.) was dissolved in THF (40 mL) and added to the LDA solution at -78 C. The solution was stirred at -78 C for 30 minutes and iodomethane (1.32 mL; 21.22 mmol; 1.05 eq.) was added. The solution was slowly warmed to room temperature and stirred at room temperature for 1 hour. Water (100 mL) was then added to the reaction followed by EtOAc (50 mL). The layers were separated and the aqueous layer was extracted with EtOAc (2 x 50 mL). The combined organic layers were dried over Na2S04, filtered, and concentrated under reduced pressure to afford the product (5.0 g, 94% yield) as an oil. The product was analytically pure and used without further purification. LC/MS m/z (M+l) 262.0, Retention time 1.78 minutes; (10-99% CH3CN-H20 gradient with 0.03% TFA, 5 min). .H NMR (400 MHz, CDC13) 8 7.24-7.14 (m, 5H), 4.08 (q, J = 7.1 Hz, 2H), 3.40 (s, 2H), 2.60-2.57 (m, 2H), 2.08-2.02 (m, 4H), 1.47-1.40 (m, 2H), 1.17 (t, J = 7.1 Hz, 3H), 1.10 (s, 3H). [0210] l-Benzyl-4-methylpiperidine-4-carboxylate (5.0 g; 19.15 mmol) was dissolved in Et20 (50 mL) and cooled to 0 C. L1AIH4 (1.0 g; 26.3 mmol) was slowly added portion-wise to the solution. After the addition was complete, the solution was slowly warmed to room temperature and stirred for 1 h. The solution was then cooled to 0 C and slowly quenched with IN NaOH (6 mL). The resultant white precipitates were filtered and washed with EtOAc (100 mL). The combined organic layers were concentrated under reduced pressure to provide the product (3.9 g, 90% yield) as an oil which was used without further purification. LC/MS m/z M+l 220.0, retention time 0.64 minutes; (10-99% CH3CN-H20 gradient with 0.03% TFA, 5 min). .H NMR (400 MHz, CDCI3) 8 7.25-7.16 (m, 5H), 3.46 (s, 2H), 3.30 (d, J= 3.9 Hz, 2H), 2.51-2.46 (m, 2H), 2.26-2.20 (m, 2H), 1.52-1.45 (m, 3H), 1.30-1.25 (m, 2H), 0.87 (s, 3H). (l-benzyl-4-methylpiperidin-4-yl)methanol (3.9 g; 17.8 mmol) was dissolved in MeOH (50 mL) and NH4CO2H (12.5 g; 178.0 mmol) was added. Pd/C (10% by weight, wet; 5.5 g) was then added and the system was flushed with nitrogen and then with hydrogen. The reaction was stirred at room temperature overnight (18 h) and then filtered through a pad of Celite. The solvent was removed under high vacuum to provide a solid that was a mixture of the amino alcohol and NH4CO2H. The crude product (2.4 g as a mixture with NH4COOH) was used in the next step without further purification. LC/MS m/z (M+l) 130.0, retention time 0.35 min; (10-99% CH3CN-H2O gradient with 0.03% TFA, 5 min). .H NMR (400 MHz, CDCI3) 5 3.17 (s, 2H), 3.03-2.98 (m, 2H), 2.95-2.88 (m, 2H), 1.64-1.57 (m, 2H), 1.36-1.31 (m, 2H), 0.89 (s, 3H). [0212] (4-methylpiperidin-4-yl)methanol (2.4 g, a mixture of the amino alcohol andNELtCC^H) was suspended in DCM (70 mL). Et3N (5 mL; 37.2 mmol) was then added followed by the drop-wise addition of ethyl chloroformate (1.05 mL, 13 mmol, 1.4 eq.). After 1 hour at room temperature, IN HC1 (70 mL) was added and the layers were separated. The aqueous layer was extracted with DCM (70 mL) and the combined organic layers were dried over Na2S04, filtered, and concentrated under high vacuum. The product (1.7 g, 47% yield over 2 steps) is obtained analytically pure as an oil and used without further purification. LC/MS m/z (M+l) 202.2, retention time 1.89 minutes; (10-99% CH3CN-H2O gradient with 0.03% TFA, 5 min). .H NMR (400 MHz, DMSC-d6) 8 4.05 (q, J= 7.1 Hz, 2H), 3.66 (dt, J = 13.6,4.7 Hz, 2H), 3.32 (s, 2H), 3.11 (t, .7=5.2 Hz, 1H),3.11 (dd, .7=23.9, 3.5 Hz, 1H), 1.44-1.37 (m, 3H), 1.26-1.22 (m, 2H), 1.19 (t, J= 7.1 Hz, 3H), 0.93 (s, 3H).[0213] To a 100 mL round bottom flask was added DCM (30 mL) and oxalyl chloride (0.88 mL; 10.13 mmol). The solution was cooled to -78 C and treated with DMSO (1.19 mL; 16.88 mmol). The solution was stirred at -78 C for 20 minutes and then treated with ethyl 4-(hydroxymethyl)-4-methylpiperidine-l-carboxylate (1.7 g; 8.44 mmol, dissolved in 10 mL of DCM). The solution was stirred for 30 minutes at -78 C and then treated with Et3N (3.53 mL; 25.32 mmol). The solution was stirred at -78 C for 20 min and then slowly warmed to room temperature and stirred at room temperature for an additional 2 h. The solution was then treated with saturated aqueous NaHCC>3 (50 mL), diluted with DCM (50 mL), and the layers were separated. The organic layer was washed with brine (50 mL), dried over Na2SC>4, filtered, and concentrated under reduced pressure to afford 1.6 g (95% yield) of the product as an oil which was used without further purification. LC/MS m/z (M+l) 200.0, retention time 2.23 minutes; (10-99% CH3CN-H2O gradient with 0.03% TFA, 5 min). .H NMR (400 MHz, CDC13) 5 9.40 (s, 1H), 4.06 (q, J= 7.1 Hz, 2H), 3.66 (dt, J…

297172-16-8, The synthetic route of 297172-16-8 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; VERTEX PHARMACEUTICALS, INCORPORATED; WO2006/23852; (2006); A2;,
Piperidine – Wikipedia
Piperidine | C5H11N – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.10315-06-7,Methyl 1-benzylpiperidine-4-carboxylate,as a common compound, the synthetic route is as follows.

Synthesis of the intermediate compound 6 was carried out according to the previously reported procedure [37] . n-Butyllitium solution (19 mL, 1.6 M in hexane) was added to 6.8 g of 4-bromobenzotrifluride 2 (30 mmol) in diethyl ether. To this mixture 2.4 g (10 mmol) of methyl-1-benzylpiperidine-4-carboxylate 1 were added dropwise at 5 C. The reaction mixture was stirred at room temperature for 1 h and at 45 C for 2 h. The crude product was obtained according to the reported procedures, and purified by silica gel flash column chromatography using 0-50% ethyl acetate/hexane as eluent to yield a brown solid. (4.4 g, 77% yield). 1H NMR (CDCl3): delta 7.64 (m, 8H, 2 * trifluromethylphenyl ArH), 7.33-7.30 (m, 5H, Benzyl ArH) 3.56 (s, 2H, Benzylic CH2), 3.00-2.97 (m, 2H, N-CH2-CH2), 2.54 (t, J = 11.6 Hz, 1H, N-CH2-CH2-CH), 2.10-2.07 (m, 2H, N-CH2-CH2), 1.60-1.45 (m, 4H, 2 * N-CH2). 13C NMR (CDCl3) delta 150.9, 149.6, 139.4, 128.4 (2C), 128.1 (4C), 127.3 (2C), 126.1 (2C), 125.8 (2C), 125.3 (3C), 125.2 (2C), 81.4, 62.7, 53.8 (2C), 43.8, 26.2 (2C). HRMS (ESI) m/z: calcd for C27H25F6NO [M + H]+ 494.1919; found 494.1883.

10315-06-7, The synthetic route of 10315-06-7 has been constantly updated, and we look forward to future research findings.

Reference：
Article; Kondengaden, Shukkoor M.; Luo, Liu-fei; Huang, Kenneth; Zhu, Mengyuan; Zang, Lanlan; Bataba, Eudoxie; Wang, Runling; Luo, Cheng; Wang, Binghe; Li, Keqin Kathy; Wang, Peng George; European Journal of Medicinal Chemistry; vol. 122; (2016); p. 382 – 393;,
Piperidine – Wikipedia
Piperidine | C5H11N – PubChem

4629-80-5,With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.4629-80-5,1,3-Dimethylpiperidin-4-one,as a common compound, the synthetic route is as follows.

EXAMPLE 14 6-chloro-3-(1,3-dimethyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-indole Beginning with 0.97 gm (6.4 mMol) 6-chloro-1H-indole and 1.6 gm (13.0 mMol) 1,3-dimethyl-4-piperidone, 1.05 gm (63%) of the title compound were recovered as a crystalline solid. m.p.= 170-172C MS(FD): m/e=260 (M+) EA: Calculated for: C15H17N2Cl: Theory: C, 69.09; H, 6.57; N, 10.74. Found: C, 69.39; H, 6.40; N, 10.97.

As the paragraph descriping shows that 4629-80-5 is playing an increasingly important role.

Reference：
Patent; ELI LILLY AND COMPANY; EP812826; (1997); 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.39514-19-7,Ethyl 1-benzyl-3-oxopiperidine-4-carboxylate,as a common compound, the synthetic route is as follows.

STEP A: l -Benzyl-3-oxo-piperidine-4-carboxylic acid ethyl ester (5.0 g, 16.8 mmol) was stirred in dry ethanol (55 mL). The flask was evacuated and filled with nitrogen prior to the addition of 10percent Pd/C ( 1 .0 g). The resulting suspension was stirred for 16 hours under an atmosphere of hydrogen. The reaction mixture was filtered through Celite and concentrated to afford a yellow solid (2.9 g). This was immediately dissolved in CH2C12 (100 mL), treated with Boc-anhydride (4.4 g, 20.2 mmol) and DIPEA (4.3 g, 33.6 mmol), and stirred for 16 hours at room temperature. The organics were washed sequentially with HCI (IN), water and brine, dried over magnesium sulfate, filtered, and concentrated to afford 3-oxo-piperidine-l ,4-dicarboxylic acid 1 -te -butyl ester 4-ethyl ester as a clear oil (4.8 g, 100percent yield). MS (ESI) m/e (M+H+): 271.36, 39514-19-7

As the paragraph descriping shows that 39514-19-7 is playing an increasingly important role.

Reference：
Patent; NOVARTIS AG; MILLER-MOSLIN, Karen; TOURE, Bakary-Barry; VISSER, Michael Scott; YUSUFF, Naeem; WO2011/29842; (2011); 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

Add 20 mg of calcium hydride as a desiccant to a dry 10 ml reaction tube. Nitrogen is introduced to create an oxygen-free environment for the reaction system. Take 1-ethylpiperidin-4-ol (154 mg, 1.2 mmol), Alizarin yellow R (5 mol%) was dissolved in 1.5 ml of acetonitrile and syringe was inserted into the reaction tube. After stirring for 20 minutes, 2-naphthalenesulfonyl chloride (227 mg, 1.0 mmol) was dissolved in 1.5 ml of acetonitrile and injected into the reaction system with a syringe. The reaction was carried out under a normal temperature of 30 W for 24 hours. The organic layer was extracted with ethyl acetate (20 mL×3×). The solvent was evaporated under reduced pressure, and the product was obtained by flash column chromatography to afford 232 mg (yield: 80%).

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

Reference：
Patent; Northwest Normal University; Fu Ying; Shi Chunzhao; Xu Qinshan; (8 pag.)CN110204465; (2019); A;,
Piperidine – Wikipedia
Piperidine | C5H11N – PubChem

3612-20-2, 1-Benzylpiperidin-4-one is a piperidines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a solution of ammonium chloride (1.73 g, 32.3 mmol) in water (20 ml) is added a 30% ammonia solution (2 ml) followed by 1-benzyl-4-piperidone. After 20 minutes sodium cyanide (1.47 g, 30 mmol) is added portionwise over 15 minutes. After stirring for one hour, water (50 ml) is added and the products are extracted with DCM (3*50 ml), dried (MgSO4) filtered and concentrated in vacuo. Purification by chromatography on silica eluding with 50-100% EtOAc in iso-hexane affords 4-Aminomethyl-1-benzyl-piperidine-4-ylamine; [M+H]+ 216, 3612-20-2

The synthetic route of 3612-20-2 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; Novartis AG; US2010/130506; (2010); A1;,
Piperidine – Wikipedia
Piperidine | C5H11N – PubChem

5274-99-7, 1-Benzoylpiperidine-4-carboxylic acid is a piperidines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

A mixed solution of methyl (2RS, 3SR)-2-amino-3-(1H-indol- 3-yl) butanoate (4.65 g), 1-benzoylpiperidine-4-carboxylic acid (5.13 g), WSC (5.75 g) and HOBt (4.60 g) in tetrahydrofuran (70 ML) WAS stirred at room temperature for 12 hrs. The reaction solution was diluted with ethyl acetate, a saturated aqueous sodium carbonate solution was added and the mixture was subjected to extraction. The organic layer was dried (MGS04) and the solvent was evaporated. The residue was purified by silica gel column chromatography (developing solvent: hexane/ethyl acetate = 1/1-ethyl acetate) to give the title compound as a pale yellow oil (7.86 g, yield 88%). 1H NMR (300 MHz, CDCl3) 8 ppm: 1.47 (d, J = 6.9 Hz, 3 H), 1.63 – 1. 83 (m, 4 H), 2.27-2. 35 (m, 1 H), 2.80-3. 00 (m, 2 H), 3.62-3. 78 (m, 4 H), 4.60 (brs, 1 H), 4.86-4. 96 (m, 1 H), 5.86-6. 02 (m, 1 H), 6.99 (d, J = 3.6 Hz, 1 H), 7.08-7. 20 (m, 2 H), 7.33-7. 40 (m, 6 H), 7.55-7. 60 (m, 1 H), 8.22- 8.28 (m, 1 H)., 5274-99-7

5274-99-7 1-Benzoylpiperidine-4-carboxylic acid 78935, apiperidines compound, is more and more widely used in various fields.

Reference：
Patent; TAKEDA CHEMICAL INDUSTRIES, LTD.; WO2004/46107; (2004); A1;,
Piperidine – Wikipedia
Piperidine | C5H11N – PubChem