Tag: M.W:200-300

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.149554-03-0,tert-Butyl 2-(4-oxopiperidin-1-yl)acetate,as a common compound, the synthetic route is as follows.

To a mixture of Example 87D (0.200 g, 0.505 mmol) and triethylamine (0.155 mL, 1.1 10 mmol), acetic acid (0.144 mL, 2.52 mmol) in dichloromethane (3 mL) and methanol (3 mL) was added tert-butyl 2-(4-oxopiperidin- 1 -yl)acetate (0.215 g, 1.009 mmol) and MP-cyanoborohydride (Biotage, 81 1 mg, 2.019 mmol). The reaction mixture was heated at 40C for 3 hours. The solid material was filtered and rinsed with dichloromethane and methanol. The filtrate was concentrated. The residue was partitioned in ethyl acetate and saturated aqueous sodium bicarbonate. The organic layer was washed with brine, dried over anhydrous sodium sulfate, filtered, and concentrated until most solvent was evaporated. The precipitates were filtered, washed with cold ethyl acetate, and vacuum oven-dried to provide the title compound. MS (ESI+) m/z 521.1 (M+H)+.

149554-03-0, As the paragraph descriping shows that 149554-03-0 is playing an increasingly important role.

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;,
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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

[(3S,4R)-4-(4-Fluoro-phenyl)-piperidin-3-yl]-methanol (3.00 g, 14.3 mmol, 1 equiv) was suspended in CH2Cl2 (10 mL) and Boc anhydride (3.23 g, 14.8 mmol, 1.03 equiv) was added. This was stirred for 2 h then concentrated to give the crude, which was used in the next reaction without further purification. [

125224-43-3, As the paragraph descriping shows that 125224-43-3 is playing an increasingly important role.

Reference：
Patent; CHEMOCENTRYX, INC.; FAN, Junfa; KALISIAK, Jaroslaw; LUI, Rebecca, M.; MALI, Venkat, Reddy; MCMAHON, Jeffrey, P.; POWERS, Jay, P.; TANAKA, Hiroko; ZENG, Yibin; ZHANG, Penglie; (194 pag.)WO2016/187393; (2016); A1;,
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24666-55-5, Benzyl (2,6-dioxopiperidin-3-yl)carbamate is a piperidines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

N-CBZ-L-glutamic acid 2.81 g (0.01 mol),Urea 1.2g (0.2mol) was added to DMSO to dissolve and reflux at 150 C. After 2 h, the temperature was lowered.HCl gas, a white solid 1.518 g, a yield of 92%;, 24666-55-5

As the paragraph descriping shows that 24666-55-5 is playing an increasingly important role.

Reference：
Patent; Wang Yanping; Yang Yi; Zhang Xiaoling; Zhou Qinghe; Xu Congying; (8 pag.)CN108218833; (2018); A;,
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10315-06-7, Methyl 1-benzylpiperidine-4-carboxylate is a piperidines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Methyl l -benzylpiperidine-4-carboxylate (.50 g, 2.1 mmol) as a solution in THF (43 mL, 0.05 M) was added to a flame dried 250 mL round bottom flask containing the Weinreb amine salt (0.26 g, 2.7 mmol, 1.25 eq) and stirred at -5C. Phenethylmagnesium chloride (8.6 mL, 8.6 mmol, 4 eq) was then added dropwise and the reaction was allowed to stir until complete consumption of starting material at -5C. After formation of the Weinreb amide the reaction was slowly warmed to room temperature and tracked by LCMS. After an additional 2 hours of stirring at room temperature the reaction was quenched with NH4C1 (20 mL) and basified with 10% NaOH. The mixture was further partitioned with EtOAc and separated. The aqueous layer was extracted with DCM (3 times). The organic layers were combined, dried over anhydrous magnesium sulfate, filtered and concentrated to afford l-(l-benzylpiperidin-4-yl)-3-phenylpropan-l-one (.630 g, 96% yield). (0633) Scaleup: Conducted as described above but scaled to 5 g of starting material. Taken on crude to hydrazine reaction.HRMS calc’d for C2iH26ON 308.20089; found [M+H] 308.20037

10315-06-7, As the paragraph descriping shows that 10315-06-7 is playing an increasingly important role.

Reference：
Patent; EMORY UNIVERSITY; COX, Bryan D.; WILSON, Lawrence J.; PROSSER, Anthony; LIOTTA, Dennis C.; SNYDER, James, P.; (98 pag.)WO2015/175855; (2015); A1;,
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888952-55-4, Methyl 1-Boc-3-methylpiperidine-3-carboxylate is a piperidines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,888952-55-4

A solution of ester from Preparative Example X-910-C (1.08 g, 4.20 mmol) in EtOH (16.8 mL) at 25 C. was treated with NaOH (0.050 g, 3 equiv.). The solution was heated at 70 C. for 3 h. The solution was cooled to 25 C. and concentrated under reduced pressure. The residue was dissolved in H2O (50 mL). The aqueous layer was washed with Et2O (2×30 mL). The aqueous layer was acidified to pH=1 with 1 M HCl. The aqueous layer was extracted with Et2O (2×30 mL) and the organic layer was dried (MgSO4), filtered and concentrated under reduced pressure. The residue was used directly in the next reaction.

As the paragraph descriping shows that 888952-55-4 is playing an increasingly important role.

Reference：
Patent; Schering Corporation; US2007/82900; (2007); A1;,
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61995-20-8,61995-20-8, Benzyl 3-oxopiperidine-1-carboxylate is a piperidines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a solution of Compound 1 (5.0 g, 21.5 mmol) and ethyl 2-diazoacetate (3.2 g, 28.1 mmol) in THF (100 mL) was added BF3-Et2O (2.7 mL, 21.5 mmol) at -78 C. under N2. The reaction mixture was stirred at -78 C. for 1.5 h, then warmed to 28 C. slowly and stirred for 1.5 h. The resulting mixture was quenched with NaHCO3 (sat.) and extracted with EA (300 mL). The organic layer was dried over Na2SO4 and concentrated in vacuo to give a crude product, which was purified by flash column chromatography to give a mixture of Compound 2 and 3 (3.4 g, 50%). LCMS: 320.0 [M+1]. To a suspension of NaH (338 mg, 8.5 mmol) in THF (30 mL) was added a solution of a mixture of Compound 3 and Compound 3?(2.7 g, 8.5 mmol) in THF (30 mL) at 0 C. under N2, and stirred at rt for 0.5 h. A solution of Select F (2.7 g, 8.5 mmol) in DMF (15 mL) was added dropwise. The reaction mixture was stirred at r.t. for 3 h. The resulting mixture was quenched with NH4Cl and extracted with EA (200 mL). The organic layer was washed with brine, dried over Na2SO4 and concentrated in vacuo to give the crude product, which was purified by flash column chromatography to give Compound 4 (1.0 g, 35%) and Compound 4? (0.9 g, 32%). Compound 4: 1H NMR (400 MHz, CDCl3) delta=7.28-7.39 (m, 5H), 5.18 (s, 2H), 4.40-4.68 (m, 1H), 4.11-4.39 (m, 3H), 3.45-3.63 (m, 1H), 3.21-3.38 (m, 1H), 1.85-2.45 (m, 4H), 1.26-1.30 (m, 3H). Compound 4?: 1H NMR (400 MHz, CDCl3) delta=7.28-7.40 (m, 5H), 5.14-5.18 (m, 2H), 4.24-4.47 (m, 4H), 3.88-4.00 (m, 1H), 3.09-3.25 (m, 1H), 2.85-2.91 (m, 2H), 1.92-1.95 (m, 2H), 1.27-1.35 (m, 3H).

As the paragraph descriping shows that 61995-20-8 is playing an increasingly important role.

Reference：
Patent; Novira Therapeutics, Inc.; Hartman, George D.; US2015/225355; (2015); A1;,
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189333-49-1, 3-Benzyl-3,9-diazaspiro[5.5]undecane is a piperidines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Formaldehyde solution (27.25 g, 335.75 mmol, 25.00 mL, 37% purity), Sodium triacetoxyborohydride (17.52 g, 82.66 mmol) and glacial acetic acid (7.45 g, 123.99 mmol, 7.10 mL) were added separately into the compound I2-A (10.10 g, 41.33 mmol) in methanol (150.00 mL) solution, and was stirred at 20-25C for 2 hours, the solvent was concentrated, 10% NaOH solution was used to adjust the pH to around 8, then extracted by dichloromethane 800 mL (150 mL ×6), the organic phase was washed by saturated brine 300 mL, dried over anhydrous sodium sulfate, then filtered and concentrated to give the compound 32-A. MS m/z: 259.1[M+H]+, 189333-49-1

Big data shows that 189333-49-1 is playing an increasingly important role.

Reference：
Patent; Shijiazhuang Sagacity New Drug Development Co., Ltd.; QIAN, Wenyuan; YANG, Chundao; LI, Zhengwei; LI, Jie; LI, Jian; CHEN, Shuhui; (137 pag.)EP3572413; (2019); A1;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.191732-76-0,5-Amino-2-(2,6-dioxopiperidin-3-yl)isoindoline-1,3-dione,as a common compound, the synthetic route is as follows.

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 muL, 0.220 mmol, 2 equiv) in THF (1.8 mL, 0.1 M) was heated to reflux overnight. The reaction mixture was filtered, and the filter cake was washed with Et2O to give the title compound as a white solid (27 mg, 47%), that was used without further purification.1H NMR (500 MHz, DMSO-d6) delta 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 C15H14N3O5 [M+H]+ 316.09, found 316.23., 191732-76-0

As the paragraph descriping shows that 191732-76-0 is playing an increasingly important role.

Reference：
Patent; DANA-FARBER CANCER INSTITUTE, INC.; BUCKLEY, Dennis; WINTER, Georg; PHILLIPS, Andrews, J.; HEFFERNAN, Timothy, P.; BRADNER, James; ROBERTS, Justin; BEHNAM, Nabet; (544 pag.)WO2018/148443; (2018); A1;,
Piperidine – Wikipedia
Piperidine | C5H11N – PubChem

710972-40-0, tert-Butyl 4-((2-methoxyethyl)amino)piperidine-1-carboxylate is a piperidines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

tert-Butyl 4-[(2-methoxyethyl)amino]piperid me-i -carboxylate (300 mg, 1 .16 mmol) wasdissolved in THF (10 mL) and treated with N-methyl-2-pyrrolidinone (344 mg, 3.48 mmol) andtriethylamine (0.7 mL, 4.65 mmol). The reaction mixture was stirred at 70 C for 1 h, then Intermediate 108, 2,2,2-trifluoroethyl trifluoromethanesulfonate (297 mg, 1.28 mmol) was added dropwise at 25 C. The resulting reaction mixture was stirred at 70 C for 16 h. The solvents were removed in vacuo and the reaction mixture was partitioned between H20 (120mL) and EtOAc (100 mL). The aqueous layer was further extracted with EtOAc (2 x 100 mL), and the combined organic layers were dried (Na2SO4). The solvent was removed in vacuo and residue was purified by column chromatography (Normal neutral activated alumina, at 10 % to20 % EtOAc in hexane) to give tert-butyl 4-[(2-methoxyethyl)(2,2,2-trifluoroethyl)amino]piperidine-1-carboxylate (180 mg, 46 %) as a gum. LCMS (Method I): mlz 341 (M+H) (ES), at 5.31 mi UV active., 710972-40-0

710972-40-0 tert-Butyl 4-((2-methoxyethyl)amino)piperidine-1-carboxylate 43652134, apiperidines compound, is more and more widely used in various fields.

Reference：
Patent; HEPTARES THERAPEUTICS LIMITED; BROWN, Giles Albert; CONGREVE, Miles Stuart; PICKWORTH, Mark; TEHAN, Benjamin Gerald; (117 pag.)WO2017/21730; (2017); A1;,
Piperidine – Wikipedia
Piperidine | C5H11N – PubChem

109384-19-2, tert-Butyl 4-hydroxypiperidine-1-carboxylate is a piperidines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Example 9 4- (1-Benzyl-piperidin-4-yloxy)-benzamide Step 1 4- (4-Cyano-phenoxy)-piperidine-1-carboxylic acid tert-butyl ester Add a solution of N-Boc-4-hydroxypiperidine (3.0 g, 14.9 mmol) in DMF (5 mL) to a suspension of sodium hydride (894 mg, 22.4 mmol) in DMF (17 mL). Stir the reaction mixture while heating at 50C for 45 min. Then add a solution of 4-fluoro- benzonitrile (2.16 g, 17.9 mmol) in DMF (5 mL). Stir and heat at 50C for 2h. Let cool to room temperature and quench with water (0.5 mL). Evaporate DMF. Redissolved the resulting residue in EtOAc/hexanes (2/1,20 mL) and wash with water (3×15 mL). Dry the organic layer over magnesium sulfate, filter and concentrate. Purify by chromatography (EtOAc/hexanes 20% and EtOAc/hexanes 10%) to yield the title compound (2.32 g, 52%).

109384-19-2, The synthetic route of 109384-19-2 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; ELI LILLY AND COMPANY; WO2005/61442; (2005); A1;,
Piperidine – Wikipedia
Piperidine | C5H11N – PubChem