Category: piperidines

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.71985-80-3,1-Methylpiperidine-4-carboxylic acid hydrochloride,as a common compound, the synthetic route is as follows.,71985-80-3

48 mg (0.26 mmol) 1-methyl-piperidine-4-carboxylic acid hydrochloride were dissolved in 5 ml thionyl chloride and heated to reflux for 30 min. The excess thionyl chloride was removed by evaporation and the resulting acid chloride dissolved in 5 ml methylene chloride. This solution was added to a solution of 100 mg (0.25 mmol) 3-(3-amino-4-trifluormethoxy-phenyl) -5,5-dimethyl-1-pyridin-4-ylmethyl-imidazolidine-2,4-dione and 111 mg (0. 68mmol) huenig’s base and the mixture was stirred overnight at RT and heated to reflux for 1h. The mixture was poured on saturated sodium bicarbonate solution, extracted with ethylacetate, then dried and evaporated. The residue was was purified by preparative HPLC. (C18 reversed phase column, elution with a water (0.1% trifluoracetic acid) /acetonitrile gradient) Yield: 10 mg MS(ES+): m/e = 520 LC/MS Retention time [min] = 0.86

As the paragraph descriping shows that 71985-80-3 is playing an increasingly important role.

Reference：
Patent; Aventis Pharma S.A.; EP1621536; (2006); A1;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.888952-55-4,Methyl 1-Boc-3-methylpiperidine-3-carboxylate,as a common compound, the synthetic route is as follows.

Example 2 – Preparation of Intermediate 2 The synthesis of Intermediate 2 followed the procedure of General Procedure 2 following. Intermediate 1 Intermediate 2 To a cold solution (-78C) of acetonitrile (1.67 g, 40.8 mmol, 1.5 eq) in tetrahydrofuran (70 mL) was added n-BuLi (23% in hexane, 2.61 g, 40.8 mmol, 1.5 eq) under inert N2 atmosphere over a period of 20 minutes. After completion of addition, the reaction was stirred for another 60 minutes. To the cold (-78C) mixture was then added Intermediate 1 (7.0 g, 27.2 mmol, 1.0 eq) in portions, and the reaction mixture was stirred for 3 hours. The reaction mixture was quenched with saturated ammonium chloride solution and the product was extracted with ethyl acetate. The organic phase was dried with sodium sulfate and concentrated under reduced pressure. The residue was purified by column chromatography using silica gel (60-120 mesh size) eluting with 10-40% ethyl acetate in n-hexane, yielding product tert-butyl 3-(2- cyanoacetyl)-3-methylpiperidine-1-carboxylate (Intermediate 2; 4.775 g, yield: 65.9%) m/z 211.0 [M-56]+ 1H NMR (400 MHz, DMSO) delta 4.26 (q, J = 20.1 Hz, 2H), 3.74 (d, J = 12.6 Hz, 1H), 3.38-3.32 (m, 1H), 3.21- 3.06 (m, 2H), 1.94- 1.77 (m, 1H), 1.56- 1.31 (m, 12H), 1.06 (s, 3H) ppm., 888952-55-4

888952-55-4 Methyl 1-Boc-3-methylpiperidine-3-carboxylate 46911995, apiperidines compound, is more and more widely used in various fields.

Reference：
Patent; VERSEON CORPORATION; SHORT, Kevin Michael; ESTIARTE-MARTINEZ, Maria de los Angeles; KITA, David Ben; SHIAU, Timothy Philip; (340 pag.)WO2016/138532; (2016); A1;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.162166-99-6,1-Boc-3-Methanesulfonyloxymethyl-piperidine,as a common compound, the synthetic route is as follows.

tert-butyl 3-(methylsulfonyloxymethyl)piperidin-1-carboxylate (0.41 g, 1.4 mmol) obtained in Step B was dissolvedin 7 mL of DMF. Sodium cyanide (0.075 g, 1.54 mmol) was added thereto, and the mixture was stirred at 60Cfor 16 hours. The reaction solution was concentrated under reduced pressure, diluted with water, and extracted withEtOAc. The organic layer was separated and dried with MgSO4 to obtain the title compound (0.29 g, 93 %).1H-NMR (CDCl3) delta 3.90 (1H, m), 3.82 (1H, m), 2.92 (2H, m), 2.30 (2H, m), 1.92 (2H, m), 1.68 (1H, m), 1.49 (1H, m),1.46 (9H, s), 1.35 (1H, m), 162166-99-6

As the paragraph descriping shows that 162166-99-6 is playing an increasingly important role.

Reference：
Patent; LG Chem, Ltd.; KIM, Young Kwan; PARK, Sang Yun; JOO, Hyun Woo; CHOI, Eun Sil; PAEK, Seung Yup; KANG, Seung Wan; KIM, Byung Gyu; LEE, Chang Seok; KIM, Sung Wook; LEE, Sang Dae; (369 pag.)EP3239143; (2017); A2;,
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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: To a mixture of NaH (146mg, 6.08mmol) in THF (2mL) was added a solution of intermediate 11 (500mg, 1.52mmol) in THF (4mL) at 0C, and the mixture was stirred for 40min under argon. And a solution of corresponding substituted benzaldehydes (2-1b-m, 1.52mmol) in THF (1mL) was added dropwise. Then the mixture was stirred for another 4-7h under argon. After the reaction was completed, the mixture was quenched with 3mol/L HCl and basified with saturated aqueous solution of Na2CO3. Then the mixture was extracted with ethyl acetate (15mL×3) and the combined organic phases were washed with brine, dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure to provide crude product, the crude product was purified on silica chromatography to afford corresponding target compounds 12b-m.

10338-57-5, As the paragraph descriping shows that 10338-57-5 is playing an increasingly important role.

Reference：
Article; Cao, Zhongcheng; Deng, Yong; Li, Wei; Shi, Yichun; Song, Qing; Yang, Xia; Zhang, Li; Bioorganic Chemistry; vol. 97; (2020);,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.20691-89-8,1-Methyl-4-piperidinemethanol,as a common compound, the synthetic route is as follows.

To Example 60 (0. 78 g, 6 mmol) was added thionyl chloride (10 mL) and the mixture was heated to reflux for about 2 hours. The mixture was cooled and concentrated to dryness. The residue was washed with acetone, suspended in saturated aqueous sodium carbonate and extracted with dichloromethane. The combined organic extracts were dried (Na2SO4), filtered and concentrated under vacuum to provide the desired product. MS (ESI) : m/z 148 (M+H) +.

20691-89-8, The synthetic route of 20691-89-8 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; ABBOTT LABORATORIES; MAKOTO, Aoyama; WO2005/95387; (2005); A1;,
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1187173-43-8, 2,7-Diazaspiro[4.5]decan-1-one hydrochloride is a piperidines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

2,7-Diazaspiro[4.5]decan-1 -one hydrogen chloride (100 mg, 0.524 mmol) was dissolved in dichloromethane (10 mL) and triethylamine (0.219 mL, 1 .573 mmol), and 2,5-bis(trifluoromethyl)benzenesulfonyl chloride (197 mg, 0.629 mmol) was added. After stirring for 17 h the reaction mixture was concentrated in vacuo and the resulting residue was purified by MDAP to give 7-{[2,5-bis(trifluoromethyl)phenyl]- sulfonyl}-2,7-diazaspiro[4.5]decan-1 -one (96 mg, 0.221 mmol, 42% yield) as a white solid. 1 H NMR (400 MHz, DMSO-d6) delta ppm 1 .46 – 1 .63 (m, 3 H) 1.66 – 1 .75 (m, 1 H) 1 .85 – 2.03 (m, 2 H) 2.72 – 2.78 (m, 1 H) 2.80 (d, J=12.28 Hz, 1 H) 3.1 1 – 3.19 (m, 2 H) 3.47 (d, J=12.28 Hz, 1 H) 3.71 (d, J=1 1 .78 Hz, 1 H) 7.75 (s, 1 H) 8.24 (s, 1 H) 8.26 – 8.33 (m, 2 H). MS ES+ve m/z 431 (M+H)., 1187173-43-8

The synthetic route of 1187173-43-8 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; CONVERGENCE PHARMACEUTICALS LIMITED; GLEAVE, Robert James; HACHISU, Shuji; PAGE, Lee William; BESWICK, Paul John; WO2011/141728; (2011); A1;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.122860-33-7,Benzyl 4-(hydroxymethyl)piperidine-1-carboxylate,as a common compound, the synthetic route is as follows.

26c. Phenylmethyl 4-formylpiperidinecarboxylate To a stirred solution of oxalyl chloride (2M solution in dichloromethane, 10.9 mL, 21.9 mmol) was added DMSO (3.1 mL, 3.4 g, 43.8 mmol) in dichloromethane (6 mL) over a period of 15 minutes. The product of Example 26b (4.4 g, 17.5 mmol) in dichloromethane (7 mL) was then added at -78 C. over a period of 15 minutes. The resultant solution was stirred at -78 C. for 1 hour and then triethylamine (12.2 mL, 8.86 g, 87.5 mmol) was added, dropwise, over a period of 15minutes. The mixture was further stirred at -78 C. for 30 min and then at 0 C. for 15 min. The reaction mixture was quenched with water and extracted with dichloromethane. The combined organic phase was washed with 1% HCl, water, dried over sodium sulfate, filtered and evaporated to give the title compound (4.4 g, 100%) which was used in the next step without purification. 1H NMR (300 MHz, CDCl3) delta9.65 (s, 1H), 7.28-7.38 (m, 5H), 5.12 (s, 2H), 4.04 (br d, J=13.1 Hz, 2H), 2.97-3.06 (m, 2H), 2.38-2.45 (m, 1H), 1.88-1.92 (m,2H), 1.52-1.64 (m, 2H). 13C NMR (75 MHz, CDCl3) delta202.7, 155.2, 136.7, 128.5, 128.6, 127.9, 67.2, 47.8, 43.0, 25.1. LRMS (APIMS) m/z 248 (MH+)., 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; Fang, Xinqin; Garvey, David S.; Gaston, Ricky D.; Lin, Chia-En; Ranatunga, Ramani R.; Richardson, Stewart K.; Wang, Tiansheng; Wang, Weiheng; Wey, Shiow-Jyi; US2003/203915; (2003); A1;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.936130-82-4,Methyl 4-(piperidin-4-yl)benzoate hydrochloride,as a common compound, the synthetic route is as follows.

936130-82-4, To a stirred solution of methyl 4- (quinidin-4-yl) benzoate (5.0 g, 22.8 mmol) andPotassium carbonate (25.0 g, 182.2 mmol) in tetrahydrofuran (50 ml) / water (50 ml) was added portionwiseDi-n-butyl dicarbonate(10.0 g, 45.8 mmol) and keep the temperature below 10 C. After adding,The reaction mixture was stirred at room temperature for an additional 0.5 hour and then diluted with water (50 ml)And extracted with ethyl acetate (50 ml x 2). The combined organic layers were washed with brine,Dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was purified by silica gel column chromatography (eluent: petroleum ether / ethyl acetate = 6/1 to 1/1) to give4- (4- (methoxycarbonyl) phenyl) piperidine-1-carboxylic acidThe third butyl ester(1.9 g, yield: 26.4%) as a white solid.

936130-82-4 Methyl 4-(piperidin-4-yl)benzoate hydrochloride 42614593, apiperidines compound, is more and more widely used in various fields.

Reference：
Patent; CHIA TAI TIANQING PHARMACEUTICAL GROUP CO., LTD.; DING, ZHAO ZHONG; WU, HAO; SUN, FEI; WU, LI FANG; YANG, LING; (97 pag.)TWI558709; (2016); B;,
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5810-56-0,With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.5810-56-0,4-Acetamidopiperidine,as a common compound, the synthetic route is as follows.

EXAMPLE 3 A mixture of 0.088 mole of 4-acetamidopiperidine, 15 g of potassium carbonate, 0.088 mole of 2-chloro-6-methoxypyridine in 100 ml of dimethylsulfoxide is heated with stirring to 130 C. for 50 hours, then it is cooled, the mixture is poured into water and the suspension thus obtained is extracted with diethyl ether. The aqueous phase is extracted with methylene chloride, the organic phase is washed with water, it is dried on anhydrous sodium sulfate and evaporated to dryness. 4-acetamido-1-(6-methoxy-2-pyridyl)piperidine is thus obtained which, after crystallisation in 95% ethanol, melts at 125 to 127 C. Yield: 43% of the theoretical.

5810-56-0 4-Acetamidopiperidine 1445156, apiperidines compound, is more and more widely used in various fields.

Reference：
Patent; Sanofi; US4409228; (1983); A;,
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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.154307-84-3,(2S,5S)-5-Hydroxypiperidine-2-carboxylic acid hydrochloride,as a common compound, the synthetic route is as follows.

Step 2 To a solution of (2S,5S)-5-hydroxypiperidine-2-carboxylic acid, HCl (0.603 g, 3.32 mmol) in 1,4-dioxane (4 mL) and water (16 mL) was added potassium carbonate (1.835 g, 13.28 mmol) followed by (9H-fluoren-9-yl)methyl carbonochloridate (0.859 g, 3.32 mmol) at 0 C. The mixture was stirred at RT for 18 hrs and then treated with water (10 ml). The resulting mixture was extracted with diethyl ether (2*15 ml). The aqueous phase was acidified with aq. HCl (1M) to pH 2-3, and extracted with DCM (3*20 ml). The combined organic layers were dried over MgSO4 and concentrated to give the crude product (2S,5S)-1-(((9H-fluoren-9-yl)methoxy)carbonyl)-5-hydroxypiperidine-2-carboxylic acid (800 mg, 65.6% yield) as a white solid. 1H NMR (500 MHz, methanol-d4) d 7.86-7.78 (m, 2H), 7.69-7.57 (m, 2H), 7.48-7.37 (m, 2H), 7.37-7.20 (m, 2H), 4.81-4.77 (m, 1H), 4.59-4.36 (m, 2H), 4.32-4.20 (m, 1H), 4.18-4.08 (m, 1H), 3.75-3.64 (m, 2H), 3.58-3.43 (m, 1H), 2.01-1.89 (m, 1H), 1.81-1.57 (m, 1H), 1.30-1.17 (m, 1H). ESI-MS(+) m/z=368.2 (M+Na), 154307-84-3

The synthetic route of 154307-84-3 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; Bristol-Myers Squibb Company; Miller, Michael Matthew; Mapelli, Claudio; Allen, Martin Patrick; Bowsher, Michael S.; Boy, Kenneth M.; Gillis, Eric P.; Langley, David R.; Mull, Eric; Poirier, Maude A.; Sanghvi, Nishith; Sun, Li-Qiang; Tenney, Daniel J.; Yeung, Kap-Sun; Zhu, Juliang; Reid, Patrick C.; Scola, Paul Michael; (892 pag.)US9308236; (2016); B2;,
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