Category: piperidines

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;,
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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;,
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63921-23-3, 1-Phenylpiperidin-4-amine is a piperidines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

This example illustrates the preparation of (1-benzyl-piperidin-4-yl)-carbamic acid 2-[7-(4-fluoro-phenoxy)-2,5-dioxo-1,2,3,5-tetrahydro-benzo[e][1,4]diazepin-4-yl]-3-methyl-butyl ester. Alcohol 63 was obtained according to steps a-e described in Example 21. Alcohol 63 (0.11 g, 0.3 mmol) in DCM (1 mL) was treated with p-nitrophenylchloroformate (0.12 g, 0.6 mmol.) and 4-methylmorpholine (0.12 g, 1.2 mmol) for 3 h at 0 C., then the reaction was quenched with sodium bicarbonate and extracted with EtOAc. The organic layer was washed with sodium bicarbonate and brine, dried and concentrated to yield 0.15 g carbonate 69, which was allowed to react with 4-amino-1-benylpiperidine to yield the title compound.

63921-23-3, As the paragraph descriping shows that 63921-23-3 is playing an increasingly important role.

Reference：
Patent; Amgen Inc.; US2006/199796; (2006); A1;,
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1445-73-4, 1-Methyl-4-piperidone is a piperidines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Step 1 Preparation of 1-methyl-4-methylaminopiperidine A mixture of 1-methyl-4-piperidone (20 g, 0.18 mol) in methanol:tetrahydrofuran (100 mL, 1:1) and methyl amine (2 M in tetrahydrofuran, 3 mole excess) was placed in a Parr shaker with 5% Pd/C and hydrogenated for two hours at 60 psi and 70 C. The catalyst was filtered and the filtrate concentrated on the rotary evaporator. The crude material was distilled at 44-45 C. at 0.3 mm Hg to give 20 g (87%) of 1-methyl-4-methylaminopiperidine. Anal. Calc’d for C7H16N2: C, 65.57; H, 12.58; N, 21.85. Found: C, 65.49; H, 12.44; N: 21,49.

1445-73-4, As the paragraph descriping shows that 1445-73-4 is playing an increasingly important role.

Reference：
Patent; G. D. Searle & Company; US6423713; (2002); B1;; ; Patent; G.D. Searle & Company; US6514977; (2003); B1;,
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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;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.236406-22-7,1-Boc-4-(Aminomethyl)-4-methylpiperidine,as a common compound, the synthetic route is as follows.

Step 4. Synthesis of 4-benzyloxycarbonylaminomethyl-1-t-butoxycarbonyl-4-methylpiperidine To 6 ml of a tetrahydrofuran solution of 4-aminomethyl-1-t-butoxycarbonyl-4-methylpiperidine, obtained by Step 3, 1 ml of diisopropylehtylamine and 0.3 ml of benzyloxycarbonyl chloride were added successively, followed by stirring for 1 hour at the same temperature. The reaction mixture was diluted with ethyl acetate, washed successively with water and brine, and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and 324 mg of the crude title compound was obtained by purifying the resulting residue by silica gel column chromatography (eluding solvent: hexane/ethyl acetate=5/1~2/1)., 236406-22-7

The synthetic route of 236406-22-7 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; Banyu Pharmaceutical Co Ltd; US6140333; (2000); A;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.358789-72-7,4-((1-Methylpiperidin-4-yl)oxy)aniline,as a common compound, the synthetic route is as follows.

Example 11 3-(2-amino-7,8-dihydropyrido[4,3-d]pyrimidin-6(5H)-yl)-N-(4-((1-methylpiperidin-4-yl)oxy)phenyl)benzamide A mixture of 3-(2-amino-7,8-dihydropyrido[4,3-d]pyrimidin-6(5H)-yl)benzoic acid (41 mg, 0.15 mmol), N,N-diisopropylethylamine (0.105 mL, 0.60 mmol), and HBTU (63 mg, 0.165 mmol) in 1.5 mL DMF was briefly warmed to approx. 50 C. to dissolve solids, then continued stirring at room temperature. After 10 minutes 4-((1-methylpiperidin-4-yl)oxy)aniline (46 mg, 0.225 mmol) was added and the reaction continued at room temperature for 3 hours. The reaction mixture was partitioned between EtOAc and aqueous NaHCO3 solution, the EtOAc layer washed with H2O, brine, dried with anhydrous Na2SO4 and rotary evaporated. The resulting solid was triturated with EtOAc to give the title compound as an off-white solid (48 mg, 70%). 1H NMR (DMSO-d6) delta: 10.02 (s, 1H), 8.13 (s, 1H), 7.60-7.67 (m, 2H), 7.49 (s, 1H), 7.30-7.40 (m, 2H), 7.20 (dt, J=7.7, 2.0 Hz, 1H), 6.90-6.96 (m, 2H), 6.40 (s, 2H), 4.28 (s, 2H), 4.26-4.35 (m, 1H), 3.64 (t, J=5.9 Hz, 2H), 2.77 (t, J=5.9 Hz, 2H), 2.56-2.66 (m, 2H), 2.17 (s, 3H), 2.10-2.21 (m, 2H), 1.86-1.97 (m, 2H), 1.55-1.69 (m, 2H)., 358789-72-7

As the paragraph descriping shows that 358789-72-7 is playing an increasingly important role.

Reference：
Patent; ALLERGAN, INC.; Hull, III, Clarence E.; Malone, Thomas C.; US2013/237538; (2013); A1;,
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Piperidine | C5H11N – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.1104083-27-3,tert-Butyl 3-hydroxy-3-methylpiperidine-1-carboxylate,as a common compound, the synthetic route is as follows.

To a solution of tert-butyl 3-hydroxy-3-methylpiperidine-1-carboxylate (0.3 g, 1.39 mmol) in MeOH (5 mL) was added 4.0 M HC1 in Dioxane (1.73 mL) at 0 C. The reaction mixture was stirred at room temperature for 4 h. After completion, volatiles were removed under reduced pressure to afford 0.15 g of 3 -methylpiperidin-3 -ol hydrochloride (Yield = 71%)., 1104083-27-3

The synthetic route of 1104083-27-3 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; THE BROAD INSTITUTE, INC.; MASSACHUSETTS INSTITUTE OF TECHNOLOGY; HOLSON, Edward; WAGNER, Florence, Fevrier; WEIWER, Michel; SCOLNICK, Edward; PALMER, Michelle; DORDEVIC, Luka; LEWIS, Michael; PAN, Jennifer, Q.; ZHANG, Yan-Ling; XU, Qihong; (425 pag.)WO2016/100940; (2016); A1;,
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3612-20-2, 1-Benzylpiperidin-4-one is a piperidines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Preparation of 1 -benzyl-N-phenylpiperidin-4-amine (Compound 7-2) [00238j To a solution of aniline (Compound 7-1, 3.72 g, 40 mmol) indichloromethane (50 mL), was added 1-benzylpiperidin-4-one (7.94 g, 42 mmol) and acetic acid (240 mg, 4 mmol). After stirred at room temperature for 2 h, sodium triacetoxyborohydride (12.72 g, 60 mmol) was added. The reaction mixture was stirred for another 1 h, then diluted with water (50 mL), neutralized to pH 7 with sodium bicarbonate, extracted with dichloromethane (100 ml x 2). The combined organic layer was washed with brine (100 ml x 2), dried over anhydrous sodium sulfate and concentrated to give 1-benzyl-N-phenylpiperidin-4-amine (Compound 7-2, 9.49 g, yield: 89%) as a white solid. MS (ES): mlz: 267[M+H]., 3612-20-2

As the paragraph descriping shows that 3612-20-2 is playing an increasingly important role.

Reference：
Patent; FANG, Qun, Kevin; SPEAR, Kerry, L.; CAMPBELL, Una; WO2014/106238; (2014); A1;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.851956-01-9,(S)-Piperidine-3-carboxylic acid hydrochloride,as a common compound, the synthetic route is as follows.

851956-01-9, A suspension of sodium borohydride (7.6 g; 200 mmol) and (S)-NPA hydrochloride(16.6 g; 100 mmol, from EXAMPLE 2) in THF (100 mL) was heated for 2 h at 700C, tillthe gas evolution ceased. The temperature was lowered to 50C and a solution of concentrated sulfuric acid (10.0 g; 100 mmol) in 40 mL of THFwas added during 30 mm. The suspension was heated to 70C for 1 h, then cooled to room temperature and carefully poured onto 20 g of cracked ice and 20 g of concentrated hydrochloric acid.The mixture was stirred overnight, basified with sodium hydroxide (40% solution in water) to pH >12, filtered and extracted three times with iso-butanol/toluene (9:11; 50 mL). Concentration under reduced pressured yielded (S)-PPM as a solid (47% yield), which had a chemical purity of 96% and an optical purity of 99.64 : 0.36.

As the paragraph descriping shows that 851956-01-9 is playing an increasingly important role.

Reference：
Patent; REUTER CHEMISCHE APPARATEBAU KG; REUTER, Karl; WEDEL, Tobias; ANDRUSHKO, Vasyl; WIEGAND, Christian; STOLZ, Florian; WO2014/173855; (2014); A1;,
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