Heterocyclic Building Blocks-piperidine

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.3970-68-1,4-Methylpiperidin-4-ol,as a common compound, the synthetic route is as follows.

(S)-1-Phenylethyl (R)-2-(4-hydroxy-4-methylpiperidin-1-yl)- 2-phenylacetate: To a solution of (S)-1-phenylethyl 2-bromo-2-phenylacetate (0.464 g, 1.45 mmol) in THF (8 mL) was added triethylamine (0.61 mL, 4.35 mmol),followed by tetrabutylammonium iodide (0.215 g, 0.58 mmol). The reaction mixture was stirred at room temperature for5 minutes and then a solution of 4-methyl-4-hydroxypiperidine (0.251 g, 2.18 mmol) in THF (2 mL) was added. Themixture was stirred for 1 hour at room temperature and then it was heated at 55-60 C (oil bath temperature) for 4 hours.The cooled reaction mixture was then diluted with ethyl acetate (30 mL), washed (H2O x2, brine), dried (MgSO4), filteredand concentrated. The residue was purified by silica gel chromatography (0-60% ethyl acetate-hexane) to provide first the (S,R)-isomer of the title compound (0.306 g, 60%) as a white solid and then the corresponding (S,S)-isomer (0.120g, 23%), also as a white solid. (S,R)-isomer: 1H NMR (CD3OD) delta 7.51-7.45 (m, 2H), 7.41-7.25 (m, 8H), 5.85 (q, J=6.6Hz, 1H), 4.05 (s, 1H), 2.56-2.45 (m, 2H), 2.41-2.29 (m, 2H), 1.71-1.49 (m, 4H), 1.38 (d, J=6.6 Hz, 3H), 1.18 (s, 3H).LCMS: Anal. Calcd. for C22H27NO3: 353; found: 354 (M+H)+. (S,S)-isomer: 1H NMR (CD3OD) delta 7.41-7.30 (m, 5H),7.20-7.14 (m, 3H), 7.06-7.00 (m, 2H), 5.85 (q, J=6.6 Hz, 1H), 4.06 (s, 1H), 2.70-2.60 (m, 1H), 2.51 (dt, J=6.6, 3.3 Hz,1H), 2.44-2.31 (m, 2H), 1.75-1.65 (m, 1H), 1.65-1.54 (m, 3H), 1.50 (d, J=6.8 Hz, 3H), 1.20 (s, 3H). LCMS: Anal. Calcd.for C22H27NO3: 353; found: 354 (M+H)+., 3970-68-1

As the paragraph descriping shows that 3970-68-1 is playing an increasingly important role.

Reference£º
Patent; Bristol-Myers Squibb Company; BELEMA, Makonen; NGUYEN, Van N.; SERRANO-WU, Michael; ST. LAURENT, Denis R.; QIU, Yuping; DING, Min; MEANWELL, Nicholas A.; SNYDER, Lawrence B.; (149 pag.)EP2328865; (2017); B1;,
Piperidine – Wikipedia
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.79098-75-2,3-Piperidin-4-yl-3,4-dihydro-1H-quinazolin-2-one,as a common compound, the synthetic route is as follows.,79098-75-2

EXAMPLE 12 1-[3,5-dibromo-N-[[4-[3,4-dihydro-2(1H)-oxoquinazolin-3-yl]-1-piperidinyl]cyanoiminomethyl]-D-tyrosyl]-4-(4-methyl-1-piperazinyl)piperidine Prepared analogously to Example 7 from N-cyanoiminodiphenylcarbonate, 3,4-dihydro-3-(4-piperidinyl)-2(1H)-quinazolinone and 1-[3,5-dibromo-D-tyrosyl]-4-(4-methyl-1-piperazinyl)-piperidine in a yield of 13% of theory. Colorless, amorphous substance. IR (KBr): 1674 (C=O), 2173 (CN) cm-1 Rf: 0.30 (eluant dichloromethane/methanol/conc. ammonia 8/2/0.2 v/v/v) ESI-MS: (M+H)+=784/786/788 (Br2)

As the paragraph descriping shows that 79098-75-2 is playing an increasingly important role.

Reference£º
Patent; Boehringer Ingelheim Pharma KG; US6313097; (2001); B1;,
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159635-22-0, tert-Butyl 3-hydroxy-4-methylenepiperidine-1-carboxylate is a piperidines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Step 2) 1-t-Butoxycarbonyl-3,4-didehydro-4-(chloromethyl)piperidine To 1-t-butoxycarbonyl-3-hydroxy-4-methylenepiperidine (5.329 g, 25.1 mmol) in toluene (120 mL) and 2,6-lutidine (3.1 mL, 26 mmol) at 0 C. was added SOCl2 (2.0 mL, 26 mmol). The reaction was heated at 40 C. for 30 min, cooled to 0 C., washed with 0 C. 1N HCl (100 mL), 0.1 N HCl (100 mL), H2 O (100 mL), brine (50 mL), dried (MgSO4), and concentrated in vacuo to afford 5.18 g (89%) of allylic chloride as a yellow oil. 1 H NMR (400 MHz, CDCl3) delta 5.78 (s, 1H), 4.04 (s, 2H), 3.95 (s, 2H), 3.55 (t, 2H, J=6 Hz), 2.24 (s, 2H), 1.45 (s, 9H) ppm.

159635-22-0, The synthetic route of 159635-22-0 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Merck & Co., Inc.; US6013652; (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.79099-07-3,1-Boc-4-Piperidone,as a common compound, the synthetic route is as follows.,79099-07-3

Prepared according to a variation of a literature procedure (J. Med. Chem., 2008, 51 , p2170): Trimethylsulfoxonium iodide (22.5 g, 102 mmol) was suspended in DME (100 mL) under N2 and potassium fe/f-butoxide (12.5 g, 1 1 1 mmol) was added. After 30 min, the mixture was cooled to 0 C and a solution of fe/f-butyl 4-oxopiperidine-1-carboxylate (20 g, 100 mmol) in DME (20 mL) was added dropwise over 45 min. The reaction was allowed to warm to RT over 16 h then quenched by the addition of water (150 mL). The mixture was extracted with Et20 (3 x 100 mL). The combined organic extracts were washed with brine (100 mL), dried over MgS04 and concentrated. The residue was dried by azeotropic distillation with toluene to give the title compound (16.5 g, 83%). 1 H NMR (300 MHz, CDCI3): delta 3.81-3.58 (m, 2H), 3.40 (ddd, 2H), 2.67 (s, 2H), 1.78 (ddd, 2H), 1.56-1.30 (m, 2H), 1.45 (s, 9H).

79099-07-3 1-Boc-4-Piperidone 735900, apiperidines compound, is more and more widely used in various fields.

Reference£º
Patent; ALMAC DISCOVERY LIMITED; HEWITT, Peter; MCFARLAND, Mary Melissa; ROUNTREE, James Samuel Shane; BURKAMP, Frank; BELL, Christina; PROCTOR, Lauren; HELM, Matthew Duncan; O’DOWD, Colin; HARRISON, Timothy; (280 pag.)WO2018/20242; (2018); A1;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.161491-24-3,1-tert-Butyl 3-methyl 4-oxopiperidine-1,3-dicarboxylate,as a common compound, the synthetic route is as follows.

In a reaction flask, methyl N-Boc-3-methylcarboxylate-4-pyridinone 25g (0.1mol) was added to methanol 300mL, then add ammonium acetate 22g (0.3mol), the reaction overnight, TLC monitoring The reaction of raw materials was complete, spin the methanol, add water 900mL, the reaction mixture was extracted three times with 300mL of dichloromethane, the combined organic phase was dried over anhydrous sodium sulfate, and dried to give a red oily liquid N-Boc-3-carboxylic acid methyl ester Amino-3-ene-piperidine 22g, 161491-24-3

161491-24-3 1-tert-Butyl 3-methyl 4-oxopiperidine-1,3-dicarboxylate 11276893, apiperidines compound, is more and more widely used in various fields.

Reference£º
Patent; Wang Huiqin; (16 pag.)CN107151247; (2017); A;,
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Piperidine | C5H11N – PubChem

1029413-55-5, tert-Butyl 4-(4-amino-1H-pyrazol-1-yl)piperidine-1-carboxylate is a piperidines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a solution of 2,4-dichioro-i ,3,5-triazine (0.62 g, 4.1 mmol) inN,N-dimethylformamide (DMF, 10 mE) at 0C. were added sequentially N,N-diisopropylethylamine (DIEA, 0.75 mE, 4.3 mmol) and tert-butyl 4-(4-amino-1H-pyrazol–yl)piperidine- 1 -carboxylate (Combi-l3locks, 1.0 g, 3.8 mmol). The mixture was allowed to warm to room temperature. The mixture was diluted with ethyl acetate and water. The aqueous phase basified with saturated aqueous sodium hydrogen carbonate solution and then was extracted thrice with ethyl acetate. The combined extracts were dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by flash chromatography (silica gel) to provide tert-butyl 4-(4-((4- chloro-i ,3,5-triazin-2-yl)amino)- 1H-pyrazol-i -yl)piperidine-i -carboxylate. ECMS-ESI (m/z): [M+H] calcd for C,5H23C1N702: 380.2. found: 379.8

1029413-55-5, As the paragraph descriping shows that 1029413-55-5 is playing an increasingly important role.

Reference£º
Patent; Gilead Sciences, Inc.; Du, Zhimin; Guerrero, Juan A.; Kaplan, Joshua A.; Knox, JR., John E.; Lo, Jennifer R.; Mitchell, Scott A.; Naduthambi, Devan; Phillips, Barton W.; Venkataramani, Chandrasekar; Wang, Peiyuan; Watkins, William J.; Zhao, Zhongdong; (593 pag.)US2016/96827; (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.154775-43-6,3-(1-(tert-Butoxycarbonyl)piperidin-4-yl)propanoic acid,as a common compound, the synthetic route is as follows.

Step (a) 3-[1-(tert-Butoxycarbonyl)piperidin-4-yl]propionic acid (4.6 g, 18 mmol), prepared as in Example 1, was dissolved in HMPA (10 mL) and THF (10 mL), and this solution was added to a -20 solution of lithium diisopropylamide (60 mmol). The mixture was warmed to 0 C., stirred for 30 minutes, and then cooled to -40 C. N-Methoxy-N-methyl-4-amino-5-chloro-2-methoxybenzamide (4.9 g, 20 mmol), prepared as in Example 2, was dissolved in HMPA (10 mL) and THF (10 mL) and this solution was added to the mixture. The mixture was allowed to warm to 0 C. over 1 hour, then diluted with water, washed with ether, acidified with hydrochloric acid, and extracted into methylene chloride. The methylene chloride extract was concentrated in vacuo and the residue was heated in an oil bath to 140 C. for 30 minutes. The mixture was cooled, partitioned between water and ethyl acetate. The ethyl acetate layer was separated, washed with 5% sodium hydroxide and then brine, dried over sodium sulfate, and evaporated. Purification by silica gel chromatography (40% ethyl acetate-hexane) gave 1-(4-amino-5-chloro-2-methoxyphenyl)-3-[1-(tert-butoxycarbonyl)piperidin-4-yl]-propan-1-one (1.5 g, 3.8 mmol), m.p. 133-134 C., 154775-43-6

As the paragraph descriping shows that 154775-43-6 is playing an increasingly important role.

Reference£º
Patent; Syntex (U.S.A.) Inc.; US5763458; (1998); A;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.188869-05-8,tert-Butyl 3-bromo-4-oxopiperidine-1-carboxylate,as a common compound, the synthetic route is as follows.

188869-05-8, General procedure: Enolate 4 (485 mg, 2.5 mmol) was stirred in EtOH (12 mL) with NH4OAc (578 mg, 7.5 mmol). After 5 min the solids had fully dissolved. At this point, chloroacetylaldehyde (50percent in H2O, 0.48 mL, 3.75 mmol) was added and the reaction was warmed to 80 ¡ãC for 1 h. Following cooling to room temperature, AcOH-H2O (4:1, 10 mL) was added and stirring was continued for 30 min. The volatiles were removed under vacuum and the residue was dissolved in CH2Cl2 and washed with H2O. The aqueous was extracted once with CH2Cl2, and the combined organics were dried over Na2SO4 and concentrated. The dark residue was purified by silica gel chromatography [heptane/EtOAc, 9:1-3:1] to give 2-formylpyrrole-3-carbonitrile (1) as an off-white solid, 153.5 mg, 51percent.

As the paragraph descriping shows that 188869-05-8 is playing an increasingly important role.

Reference£º
Article; Moss, Thomas A.; Nowak, Thorsten; Tetrahedron Letters; vol. 53; 24; (2012); p. 3056 – 3060;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.25519-78-2,(4-Fluorophenyl)(piperidin-4-yl)methanone hydrochloride,as a common compound, the synthetic route is as follows.

25519-78-2, 5-Methyl-3-phenylisooxazole-4-carboxylic acid (40 mg, 0.197 mmol), 4-(4-Fluorobenzoyl)piperidine hydrochloride (31.4 mg, 0.151 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (37.7 mg, 0.197 mmol) and triethylamine (59.8 mg, 0.591 mmol) were mixed in dichloromethane (2 ml) and stirred at room temperature over night. Solvent was evaporated in vacuo, and the residue was taken up in methanol (1 mL), filtered and purified by preparative chromatography. The fractions were partitioned between NaHCO3 (sat) and ethylacetate. The organic layer was washed with water and concentrated in vacuo to afford the title compound. HRMS (ESI, pos. ion) m/z calcd for C23H21FN2O3: 392.1536, found 392.1542.

25519-78-2 (4-Fluorophenyl)(piperidin-4-yl)methanone hydrochloride 3084438, apiperidines compound, is more and more widely used in various fields.

Reference£º
Patent; Amgen Inc.; Biovitrum AB; US2008/21022; (2008); 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.24666-56-6,3-Aminopiperidine-2,6-dione hydrochloride,as a common compound, the synthetic route is as follows.

3-Hydroxyphthalic anhydride (1.641 g, 10 mmol, 1 eq) and 3-aminopiperidine-2,6- dione hydrochloride (1.646 g, 10 mmol, 1 eq) were dissolved in pyridine (40 mL, 0.25 M) and heated to 110 C. After 14 hours, the mixture was cooled to room temperature and concentrated under reduced pressure. Purification by column chromatography (ISCO, 24 g silica column, 0-10% MeOH/DCM) afforded the desired product as a tan solid (2.424 g, 8.84 mmol, 88%)., 24666-56-6

The synthetic route of 24666-56-6 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; DANA-FARBER CANCER INSTITUTE, INC.; BUCKLEY, Dennis; BRADNER, James; REMILLARD, David Ian; (212 pag.)WO2017/223452; (2017); A1;,
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