Day: March 16, 2022

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.85908-96-9,N-Boc-2-Piperidone,as a common compound, the synthetic route is as follows.

85908-96-9, General procedure: To a solution of compounds 15, 16, 17 (2 mmol) and diphenyl phosphoryl chloride (0.62 mL, 3 mmol) in anhydrous THF (30 mL) cooled at -78 C and under nitrogen atmosphere, was added dropwise with stirring a solution of KHMDS (6 mL, 0.5 M in toluene, 3 mmol). After 30 min at -78 C, water (20 mL) was added and the resulting mixture was extracted with Et2O (2 × 50 mL) and dried over MgSO4. Evaporation of the solvent under vacuum yielded the vinyl phosphates as yellow oils, which were used directly in the next coupling step.

85908-96-9 N-Boc-2-Piperidone 7577838, apiperidines compound, is more and more widely used in various fields.

Reference：
Article; Sallio, Romain; Lebrun, Stephane; Agbossou-Niedercorn, Francine; Michon, Christophe; Deniau, Eric; Tetrahedron Asymmetry; vol. 23; 13; (2012); p. 998 – 1004;,
Piperidine – Wikipedia
Piperidine | C5H11N – PubChem

122860-33-7, Benzyl 4-(hydroxymethyl)piperidine-1-carboxylate is a piperidines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Step A: benzyl 4-(iodomethyl)piperidine-1-carboxylate (1165) A solution of I2 (9.77 g, 38.50 mmol) in THF (5 mL) was added in dropwise to a stirred solution of benzyl 4-(hydroxymethyl)piperidine-1-carboxylate (8.00 g, 32.10 mmol), 1H-imidazole (2.62 g, 38.50 mmol) and triphenylphosphine (10.10 g, 38.50 mmol) in THF (15 mL) at ambient temperature in a period of 4 hr. The reaction mixture was then quenched with water (30 mL), diluted with water (40 mL) and extracted with EtOAc (3×40 mL). The combined organic layers were washed with water (20 mL) and brine (20 mL), dried over anhydrous Na2SO4 and concentrated under reduced pressure. The residue was purified by silica gel, eluted with EtOAc/PE (1/10) to afford the title compound: LCMS (ESI) calc’d for C14H18INO2 [M+H]+: 360. found 360.

122860-33-7, 122860-33-7 Benzyl 4-(hydroxymethyl)piperidine-1-carboxylate 736490, apiperidines compound, is more and more widely used in various fields.

Reference：
Patent; Merck Sharp & Dohme Corp.; Mandal, Mihir; Tang, Haifeng; Xiao, Li; Su, Jing; Li, Guoqing; Yang, Shu-Wei; Pan, Weidong; Tang, Haiqun; DeJesus, Reynalda; Hicks, Jacqueline; Lombardo, Matthew; Chu, Hong; Hagmann, William; Pasternak, Alex; Gu, Xin; Jiang, Jinlong; Dong, Shuzhi; Ding, Fa-Xiang; London, Clare; Biswas, Dipshikha; Young, Katherine; Hunter, David N.; Zhao, Zhiqiang; Yang, Dexi; (405 pag.)US2016/333021; (2016); 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.280774-03-0,(1-Isopropylpiperidin-4-yl)methanol,as a common compound, the synthetic route is as follows.

(1) Lithium aluminum hydride (1.10 g) is suspended in tetrahydrofuran (80 ml), and thereto is added a solution of ethyl 1-isopropylpiperidine-4-carboxylate (5.00 g) obtained in Reference Example 127 in tetrahydrofuran (30 ml) dropwise under ice-cooling. The reaction solution is stirred for 2 hours under the ice-cooling, and water (1.1 ml), 15 % aqueous sodium hydroxide solution (1.1 ml) and water (3.3 ml) are added dropwise successively and stirred for additional 10 minutes. To the resulting reaction solution is added potassium carbonate, and the mixture is stirred for 20 minutes, and then the insoluble materials are removed by filtration. The filtrate is concentrated under reduced pressure, and then the resulting residue is purified by NH-silica gel column chromatography (eluent: chloroform/ethyl acetate = 1/1) to give (1-isopropylpiperidin-4-yl)methanol (4.29 g). APCI-MS M/Z:158[M+H]+.(2) Oxalyl chloride (2.0 ml) is dissolved in dichloromethane (120 ml) and thereto is added dropwise a solution of dimethylsulfoxide (3.3 ml) in dichloromethane (15 ml) under dry ice-acetone cooling. After stirring for 10 minutes under ice-cooling, a solution of (1-isopropylpiperidin-4-yl)methanol (3.00 g) obtained in Reference Example 134(1) in dichloromethane (30 ml) is added dropwise over a period of 15 minutes. After addition, the reaction solution is stirred for 2 hours under ice-cooling, and thereto is added dropwise triethylamine (13.3 ml) over a period of 10 minutes. The reaction solution is stirred for one hour while it is warmed to room temperature, and then the solution is poured to saturated aqueous sodium hydrogen carbonate solution. The mixture is extracted with dichloromethane and evaporated to remove the solvent under reduced pressure. The aqueous layer is extracted with ethyl acetate, and the extract is combined with the residue obtained by removing solvent from the above dichloromethane-extract, washed with water and saturated brine and dried over sodium sulfate. The solvent is evaporated under reduced pressure to give the crude material, 1-isopropylpiperidine-4-carbaldehyde (1.96 g). APCI-MS M/Z:156[M+H]+.(3) Triethyl phosphonoacetate (7.96 g) is dissolved in tetrahydrofuran (50 ml) and thereto is added gradually 60 % sodium hydride in oil (1.45 g) under ice-cooling. After stirring for 20 minutes under ice-cooling, to the mixture is added 1-isopropylpiperidine-4-carbaldehyde (5.03 g) obtained in Reference Example 134(2) in tetrahydrofuran (25 ml). The reaction solution is stirred for 3 hours, diluted with diethyl ether, thereto is added water and the mixture is extracted with ethyl acetate. The organic layer is washed with water and saturated brine, dried over sodium sulfate and evaporated to remove the solvent under reduced pressure. The resulting residue is purified by NH-silica gel column chromatography (eluent: n-hexane/ethyl acetate = 9/1) to give ethyl 3-(1-isopropylpiperidin-4-yl)acrylate (6.87 g). APCI-MS M/Z:226[M+H]+.(4) Ethyl 3-(1-isopropylpiperidin-4-yl)acrylate (1.01 g) obtained in Reference Example 134(3) is dissolved in ethanol (20 ml), thereto is added 2 N aqueous sodium hydroxide solution (4.5 ml) and the mixture is stirred at room temperature for 24 hours. To the reaction solution is added 2 N hydrochloric acid (9 ml), and the mixture is concentrated under reduced pressure, and then the resulting residue is lyophilized to give the title compound (1.43 g). APCI-MS M/Z:198[M+H]+., 280774-03-0

280774-03-0 (1-Isopropylpiperidin-4-yl)methanol 11147855, apiperidines compound, is more and more widely used in various fields.

Reference：
Patent; Tanabe Seiyaku Co., Ltd.; EP1489078; (2004); A1;,
Piperidine – Wikipedia
Piperidine | C5H11N – PubChem

141774-61-0, tert-Butyl (piperidin-2-ylmethyl)carbamate is a piperidines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

HATU (157 mg, 0.413 mmol)was added to a stirred solution of 2-(l -ethyl- lH-indol-2-yl)-l – methyl-lH-benzo[d]imidazole-5-carboxylic acid (110 mg, 0.344 mmol)in DMF (2 mL)followed by DIPEA (0.072 mL, 0.413 mmol). After 30 min of stirring at rt, (+l-)-tert- butyl (piperidin-2-ylmethyl)carbamate (81 mg, 0.379 mmol)was added to the reaction mixtureand this was stirred for 2 h at rt. The solvent was removed under reduced pressure and water (10 mL) was added to the residue. A cream white precipitate was filtered off and rinsed with water (2 x 5 mL). The precipitate was dried in a vacuum oven for 2 h, affording 220 mg (113%) of a cream solid (the Boc-protected product). The Boc-protected product was then taken up in DCM (5 mL)and treated with TFA (1.5 mL, 19.47 mmol). After 30 min of stirring at rt the solvent was removed under reduced pressure and the dark purple residue was loaded in MeOH on a 2 g SCX column (previously conditioned with MeOH). The column was washed with MeOH (3CV) and eluted with methanolic ammonia (2N) (3 CV). The ammonia fractions were combined and evaporated under reduced pressure. The residue (189 mg) was loaded in DCM on a 10 g SNAP silica column and purified by SP4 flash chromatography, eluting with a 0-10% methanolic ammonia (2N) in DCM(10 CV). The appropriate fractions were combined and evaporated in vacuo to give (+/-)-(2- (aminom ethyl )piperi din- 1 -yl)(2-( 1 -ethyl- lH-indol-2-yl)- 1 -methyl- lH-benzo[d]imidazol-5- yl)methanone (11.4 mg, 0.027 mmol, 7.97 % yield)as a whitesolid.LCMS (Method B): Rt = 0.80min, MH+ = 416.2., 141774-61-0

As the paragraph descriping shows that 141774-61-0 is playing an increasingly important role.

Reference：
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; AMANS, Dominique; ATKINSON, Stephen, John; BARKER, Michael, David; CAMPBELL, Matthew; DIALLO, Hawa; DOUAULT, Clement; GARTON, Neil, Stuart; LIDDLE, John; RENAUX, Jessica, Fanny; SHEPPARD, Robert, John; WALKER, Ann, Louise; WELLAWAY, Christopher, Roland; WILSON, David, Matthew; (284 pag.)WO2016/185279; (2016); 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.24666-55-5,Benzyl (2,6-dioxopiperidin-3-yl)carbamate,as a common compound, the synthetic route is as follows.

Benzyl (2,6-dioxopiperidin-3-yl)carbamate (100 g; obtained in Step b) was added to methanol (1000 mL) and the mixture was heated at 50C to 55C to obtain a clear solution. The solution was cooled to 25 C to 30C and then 10% Palladium on carbon (10 g; 50% wet) was added. The solution was hydrogenated with 3.0 kg/cm2 to 3.5 kg/cm2 hydrogen pressure at 25 C to 30C for 2 hours to 3 hours. The catalyst was removed by filtration. Concentrated hydrochloric acid (100 mL) was added to the filtrate and then stirred for 60 minutes to 90 minutes at 25C to 30C. The reaction mixture was concentrated at 40C to 45 C under reduced pressure. Methanol (100 mL) was added to the residue and then stirred for 60 minutes at 10C to 15C to obtain a slurry. The slurry was filtered and the wet solid obtained was dried at 50C under reduced pressure to obtain the title compound. (0073) Yield: 56 g (90%), 24666-55-5

The synthetic route of 24666-55-5 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; SUN PHARMACEUTICAL INDUSTRIES LIMITED; BARMAN, Dhiren Chandra; RAM, Sita; RAJBANGSHI, Mantu; NATH, Asok; PRASAD, Mohan; (14 pag.)WO2018/154516; (2018); A1;,
Piperidine – Wikipedia
Piperidine | C5H11N – PubChem

191732-76-0, 5-Amino-2-(2,6-dioxopiperidin-3-yl)isoindoline-1,3-dione is a piperidines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

In a 4 mL glass vial, a mixture of 5-amino-2-(2,6-dioxopiperidin-3-yl)isoindoline-1,3- dione(30 mg, 0.110 mmol, 1 equiv) and acetyl chloride (26 pL, 0.220 mmol, 2 equiv) in THF (1.8mL, 0.1 M) was heated to reflux overnight. The reaction mixture was filtered, and the filter cake was washed with Et20 to give the title compound as a white solid (27 mg, 47%), that was used without further purification. ?HNMR(500 MHz, DMSO-d6) 11.11 (s, 1H), 10.63 (s, 1H), 8.24 (d, J 1.5 Hz, 1H), 7.91 -7.83 (m, 2H), 5.11 (dd, J 12.8, 5.4 Hz, 1H), 2.88 (ddd, J= 17.0, 13.8, 5.4 Hz, 1H), 2.63 -2.46 (m, 2H), 2.13 (s, 3H), 2.09-2.00 (m, 1H); MS (ESI) calcd for C15H14N305[M+H] 316.09, found 316.23.

191732-76-0, 191732-76-0 5-Amino-2-(2,6-dioxopiperidin-3-yl)isoindoline-1,3-dione 9816958, apiperidines compound, is more and more widely used in various fields.

Reference：
Patent; DANA-FARBER CANCER INSTITUTE, INC.; BRADNER, James; ROBERTS, Justin; BEHMAN, Nabet; WINTER, Georg; PHILLIPS, Andrews, J.; HEFFERNAN, Timothy, P.; BUCKLEY, Dennis; (617 pag.)WO2018/148440; (2018); A1;,
Piperidine – Wikipedia
Piperidine | C5H11N – PubChem

236406-22-7, 1-Boc-4-(Aminomethyl)-4-methylpiperidine is a piperidines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a 0 oC solution of tert-butyl 4-(aminomethyl)-4-methylpiperidine-1- carboxylate (7.0 g, 30.66 mmol), NaHCO3 (3.86 g, 45.99 mmol) in ethanol (131 mL) and water (92 mL) was added benzyl chloroformate (4.4 mL, 30.66 mmol). The reaction mixture was stirred at room temperature for 2 hours and most of ethanol was removed under reduced pressure. The resulting mixture was extracted with Et2O (3 x 100 mL). Combined organic layers were washed with brine, dried over anhydrous MgSO4, filtrated and the volatiles were removed under reduced pressure. The resulting residue was purified on a silica gel pad (20 to 30% gradient of EtOAc/hexanes) to give tert-butyl 4-((benzyloxycarbonylamino)methyl)-4- methylpiperidine-1-carboxylate (9.78 g, 88% yield) as a yellowish oil.1H NMR (500 MHz, CDCl3) delta ppm 7.41- 7.29 (m, 5H), 5.17- 5.05 (m, 2H), 4.79 (br. s, 1H), 3.70- 3.58 (m, 2H), 3.22- 2.99 (m, 4H), 1.45 (s, 9H), 1.42- 1.35 (m, 2H), 1.31- 1.23 (m, 2H), 0.94 (s, 3H). MS (ES+) m/z 363 (M+1)., 236406-22-7

As the paragraph descriping shows that 236406-22-7 is playing an increasingly important role.

Reference：
Patent; RELAY THERAPEUTICS, INC.; D.E. SHAW RESEARCH, LLC; ALBRECHT, Brian K.; GIORDANETTO, Fabrizio; GREISMAN, Jack, Benjamin; MARAGAKIS, Paul; TAYLOR, Alexander M.; WALTERS, W. Patrick; (117 pag.)WO2018/57884; (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.21168-72-9,2-(4-(Aminomethyl)piperidin-1-yl)ethanol,as a common compound, the synthetic route is as follows.

[00351 ] To the solution of compound 2-(4-(aminomethyl)piperidin-1 – yl)ethanol (150 mg, 0.95 mmol) and compound 6-chloro-3-(3- (trifluoromethoxy)phenyl)imidazo[1 ,2-b]pyridazine (200 mg, 0.64 mmol) in 3 ml_ DMSO was added DIEA (0.3 ml_, 1 .37 mmol) and 10 mg CsF, the solvent was stirred for 5 h at 120 C, Then the mixture was purified by HPLC to afford the compound 2-(4-(((3-(3-(trifluoromethoxy)phenyl)imidazo[1 ,2-b]pyridazin-6- yl)amino)methyl)cyclohexyl)ethanol (34 mg, 8.2 %) as a brown solid. [00352] 1 H-NMR (CDCI3/400 MHz): delta 8.61 (s, 1 H), 8.20 – 8.25 (m, 1 H), 7.95 – 8.05 (m, 2 H), 7.66 (t, J = 4.4 Hz, 1 H), 7.21 – 7.28 (m, 1 H), 3.80 – 3.90 (m, 2 H), 3.62 – 3.75 (m, 2 H), 3.37 (d, J = 6.4 Hz, 2 H), 3.21 (t, J = 5.2 Hz, 2 H), 2.91 – 3.09 (m, 2 H), 2.10 (d, J = 14.0 Hz, 2 H), 1 .51 – 1 .69 (m, 2 H). MS (ES+, m/z): (M+H)+: 435.5.

21168-72-9, The synthetic route of 21168-72-9 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; TOLERO PHARMACEUTICALS, INC.; XU, Yong; BRENNING, Benjamin, Gary; KULTGEN, Steven, G.; LIU, Xiaohui; SAUNDERS, Michael; HO, Koc-Kan; WO2013/13188; (2013); A1;,
Piperidine – Wikipedia
Piperidine | C5H11N – PubChem

10338-57-5, 4-(Piperidin-1-yl)benzaldehyde is a piperidines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

General procedure: The 4-alkyl(aryl)aminobenzaldehyde (1 mmol) was added to(RMe2Si)3CLi, R=H,Me (1 mmol) in THF under argon. The mixturewas reacted according to Tables 1 and 2. The reaction was quenchedwith H2O, extracted with CH2Cl2 and dried over Na2SO4. The solventwas evaporated under reduced pressure and the residue was purifiedby preparative column chromatography (n-hexane/ethylacetate) andthe corresponding products were obtained.

10338-57-5, The synthetic route of 10338-57-5 has been constantly updated, and we look forward to future research findings.

Reference：
Article; Safa, Kazem Dindar; Nadimi, Sanaz; Alyari, Maryam; Journal of Chemical Research; vol. 38; 8; (2014); p. 498 – 501;,
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