Category: piperidines

7006-50-0, 4-(Methylamino)-1-benzylpiperidine is a piperidines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

7006-50-0, b) 18.9 g of 1-benzyl-4-methylaminopiperidine as the oil prepared according to a) are taken up in 250 ml of methanol and combined with 8.3 g of cyclopropanecarboxaldehyde and 11.3 g of sodium cyanoborohydride. The mixture is stirred for 5 hours at 40-50 C., then for about another 16 hours at ambient temperature. It is then acidified with 2 N hydrochloric acid, evaporated to dryness in vacuo and the residue is taken up in water. It is washed with ether, made alkaline with concentrated sodium hydroxide solution and extracted with ether/ethyl acetate. The organic extract is dried over sodium sulphate and freed from the solvents in vacuo. 22.7 g 1-benzyl-4-(cyclopropylmethyl-methyl-amino)-piperidine are obtained as a yellowish oil.

As the paragraph descriping shows that 7006-50-0 is playing an increasingly important role.

Reference：
Patent; Pairet, Michel; Pieper, Michael P.; Meade, Christopher J. M.; US2002/169181; (2002); A1;,
Piperidine – Wikipedia
Piperidine | C5H11N – PubChem

118511-81-2, 1-(Piperidin-4-yl)-1H-indole is a piperidines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,118511-81-2

A mixture of an intermediate compound 5 (prepared according to A3) (0.00057 mol), l-piperidin-4-yl-2H-indole (0.00029 mol) and PS-NaB(OAc)2H (0.001137 mol) in THF/HOAc 5% (3 ml) and N,N-dimethylformamide (3 ml) was stirred at room temperature for 16 hours and then the reaction mixture was filtered. PS-p- toluensulfonic acid (0.001137 mol) was added to the filtrate and the resulting mixture was stirred at room temperature for 16 hours. The solvent was evaporated and the resin was washed with DMF, with CH2Cl2, with CH3OH, with CH2Cl2 and with dimethyl ether. A saturated CH3OH/NH3 solution, was added to the resin and the mixture was stirred at room temperature for 16 hours, then filtered off and the filtrate was evaporated. The residue was purified by short open column chromatography over silica gel (eluent: EtOAc 100 %). The product fractions were collected and the solvent was evaporated. The residue was precipitated from CH3CN/DIPE, the resulting precipitate was collected and dried. Yield : 0.0076 g of final compound 58 (6 %; (3alpha;, 3aalpha;) racemic mixture)).

The synthetic route of 118511-81-2 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; JANSSEN PHARMACEUTICA N.V.; WO2006/56600; (2006); A1;,
Piperidine – Wikipedia
Piperidine | C5H11N – PubChem

147611-03-8, tert-Butyl 7-azaspiro[3.5]nonan-2-ylcarbamate is a piperidines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,147611-03-8

To a vial was added (2-chloropyrimidin-5-yl)boronic acid (0.049 g, 0.317 mmol), EtOH (2 mL), and tert- butyl 7-azaspiro[3.5]nonan-2-ylcarbamate (0.056 g, 0.317 mmol) followed by the addition of TEA (0.42 mL, 0.30 mmol). The contents were heated at about 95 C for about 2 h. The mixture was then added to a second vial preloaded with (5)-7-bromo-4-phenyl-3,4-dihydro-lH-benzo[4,5]imidazo[2,l-c][l,4]oxazine (0.040 g, 0.12 mmol, Preparation 24), 2M Cs2C03 (0.12 mL, 0.24 mmol), and SiliaCirf DPP-Pd (0.049 g, 0.012 mmol, 0.25 mmol/g load, SiliCycle Cat R390-100). The contents were heated at about 95 C for about 4 h, the mixture was cooled to rt and filtered through Celite. The to the filtrate was added 2 mL of 4 N HQ in 1,4-dioxane and the reaction was allowed to proceed for about 4 hours. The contents were then dried under nitrogen stream and redissolved in 50% DMSO/MeOH (2 mL). The crude material was purified by preparative HPLC (Table 1 Method k) to give the title compound (0.009 g, 9%); LC/MS (Table 1, Method f) J = 0.53 min; MS m/z: 467 (M+H)+ . (TNF IC50=A).

The synthetic route of 147611-03-8 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; ABBVIE INC.; BREINLINGER, Eric, C.; COX, Phil, B.; DAANEN, Jerome; DIETRICH, Justin; DJURIC, Stevan; DOMBROWSKI, Amanda, W.; FRANK, Kristine, E.; FRIEDMAN, Michael, M.; GOMTSYAN, Arthur; LI, Huan-Qui; LONGENECKER, Kenton; OSUMA, Augustine; ROWLEY, Ann, Marie; SCHMIDT, Robert; VASUDEVAN, Anil; WILSON, Noel; (378 pag.)WO2016/168641; (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.14813-01-5,1-Benzylpiperidin-3-ol,as a common compound, the synthetic route is as follows.,14813-01-5

Under ultrasound, 10 g of dihydropyridine main ring , i.e.,[2,6-dimethyl -4-(3-nitrophenyl)-l ,4-dihydropyridine-3,5-dicarboxylic acid monomethyl ester] was placed into 200 mL reaction flask, and 14 mL Nu,Nu-dimethylformamide (DMF) and 56 mL dichloromethane was added. To the resultant homogeneous suspension was added 2.4 mL of thionyl chloride under ice-bath, then the mixture was stirred for 1 hour to obtain a clear solution.Then, 6.3 g of pyridine (alcohol) side chain, i.e., [l-benzyl-3 -hydroxypiperidine] was added and stirred for 2.5 hours under ice-bath.The reaction solution was washed with 40 mL water (x 4) and 40 mL saturated saline solution (x 1). The dichloromethane solution was dried for two hours by adding 4 g of anhydrous sodium sulfate. Then, sodium sulfate solid was removed by filtering, and dichloromethane was recycled under reduced pressure to obtain a yellow to red crude crystal (herein after referred to as crude crystal of benidipine hydrochloride). The crude crystal mentioned above was dissolved in 100 mL acetone, and ultrasounded at 150 W and 40 MHz for 7 minutes, filtered under reduced pressure and dried to obtain 5.9 g of crystal as yellow powder (yield 36.2%)

The synthetic route of 14813-01-5 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; HEFEI BEINI MEDICAL TECHNOLOGY COMPANY, LTD; ZHANG, Zhaoyong; WO2012/142815; (2012); A1;,
Piperidine – Wikipedia
Piperidine | C5H11N – PubChem

14813-01-5, 1-Benzylpiperidin-3-ol is a piperidines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

EXAMPLE 29; Preparation of 3-(1-Naphthylsulfonyl)-5-(piperidin-3-yloxy)-1H-indazole; 1-Benzyl-3-(4-nitrophenoxy)piperidine; A mixture of 1-benzyl-3-hydroxypiperidine (2.0 g, 10 mmoles), p-fluoronitrobenzene (1.06 ml, 12 mmoles) and sodium hydride (0.285 g, 12 mmoles) in DMF was stirred at room temperature for 3 hours, diluted with H2O and extracted with EtOAc. The extracts were combined, washed sequentially with water and brine, dried over Na2SO4 and concentrated under vacuum. The resultant residue was purified by flash chromatography using as eluent 50% EtOAc/hexane to afford the title compound (3.0 g, 9.43 mmoles).

14813-01-5, The synthetic route of 14813-01-5 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; Wyeth; US2007/54896; (2007); 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.5810-56-0,4-Acetamidopiperidine,as a common compound, the synthetic route is as follows.

5810-56-0, EXAMPLE 4 A mixture of 12.5 g of 4-acetamidopiperidine, 15 g of potassium carbonate, 10 g of 2-chloropyridine in 100 ml of dimethylsulfoxide, is heated with stirring for 50 hours to 130 C., then it is cooled, 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 over anhydrous sodium sulfate and evaporated to dryness. Thus, 4-acetamido-1-(2-pyridyl) piperidine is obtained which, after crystallisation in isopropanol and recrystallisation in ethyl acetate, melts at 165 to 168 C. Yield: 4.7 g (24.5% of the theoretical).

The synthetic route of 5810-56-0 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; Sanofi; US4409228; (1983); A;,
Piperidine – Wikipedia
Piperidine | C5H11N – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.885279-92-5,1-Boc-1,8-diaza-spiro[4.5]decane,as a common compound, the synthetic route is as follows.

A solution of A2, HBTU (1 eq) and TEA (2 eq) in dry DMF (0.3 M) was stirred at RT for 5 minutes and then TEA (1 eq) and tert-butyl l,8-diazaspiro[4.5]decane-l-carboxylate were added. The mixture was stirred at RT for 16h. The product was purified by preparative RP- HPLC, using H2O/ ACN (0.1% TFA) as eluents. The pooled product fractions were lyophilized and the oily residue (A3) was treated with a DCM/TFA mixture (9:1) at 45 0C for Ih. After removal of the solvents under reduced pressure the oily residue was lyophilized from H2O/ ACN to afford the title compound as a colourless oil.1U NMR (300 MHz, DMSO-d6) delta: 8.70 (2H, br. s), 8.25 (IH, d, J = 7.83 Hz), 8.22-8.14 (IH, m), 7.70-7.58 (2H, m), 7.44-7.35 (2H, m), 7.34-7.23 (2H, m), 6.20 (IH, d, J = 7.86 Hz), 5.56 (2H, s), 3.38-3.19 (4H, m), 3.18-3.03 (IH, m), 2.07 (IH, m), 2.03-1.74 (6H, m), 1.69-1.57 (2H, m). MS (ES) C25H26FN3O2 requires: 419, found: 420 (M+H)+., 885279-92-5

The synthetic route of 885279-92-5 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; ISTITUTO DI RICERCHE DI BIOLOGIA MOLECOLARE P. ANGELETTI S.P.A.; WO2009/27730; (2009); A1;,
Piperidine – Wikipedia
Piperidine | C5H11N – PubChem

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

61995-20-8, 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 mixture of compound 2 and 3 (1 g, 3.1 mmol) dissolved MeOH/H2O (10 mL/2 mL) was added KOH (0.53 g, 9.3 mmol), and heated to 55 C. for 2 h. The mixture was diluted with EA (80 mL) and washed with brine (60 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 Compound 4 (0.32 g, 42%) and Compound 5 (0.22 g, 29%). LCMS: 248.0 [M+1]. Compound 4 1H NMR (400 MHz, CDCl3) delta 7.34-7.40 (m, 5H), 5.16-5.21 (m, 2H), 4.06-4.11 (m, 2H), 3.46-3.49 (m, 2H), 2.51-2.55 (m, 2H), 1.63-1.78 (m, 4H). Compound 5 1H NMR (400 MHz, CDCl3) delta 7.34-7.39 (m, 5H), 5.14 (s, 2H), 3.62-3.69 (m, 4H), 2.62-2.71 (m, 4H), 2.75-2.81 (m, 2H).

The synthetic route of 61995-20-8 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; Novira Therapeutics, Inc.; Hartman, George D.; US2015/225355; (2015); 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.141774-61-0,tert-Butyl (piperidin-2-ylmethyl)carbamate,as a common compound, the synthetic route is as follows.

To a solution of 2-[2-[[2-(2,6-dioxo-3-piperidyl)-1,3-dioxo-isoindolin-4-yl]amino]ethoxy]ethyl methanesulfonate (500 mg, 1.14 mmol, synthesized via Steps 1-2 of Example 184) in CH3CN (20 mL) was added tert-butyl N-(2-piperidylmethyl) carbamate (488 mg, 2.28 mmol, CAS141774-61-0), NaHCO3 (287 mg, 3.41 mmol) and KI (18.9 mg, 114 umol). The mixture was stirred at 80 C. for 16 hours. On completion, the mixture was concentrated in vacuo. The residue was purified by reversed phase flash to give the title compound (450 mg, 71% yield) as yellow solid. LC-MS (ESI+) m/z 558.4 (M+H)+.

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

Reference：
Patent; Kymera Therapeutics, Inc.; Mainolfi, Nello; Ji, Nan; Kluge, Arthur F.; Weiss, Matthew M.; Zhang, Yi; (1443 pag.)US2019/192668; (2019); 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.122860-33-7,Benzyl 4-(hydroxymethyl)piperidine-1-carboxylate,as a common compound, the synthetic route is as follows.

To oxalyl chloride (10.3 mL, 0.120 mol) in 150 mL of DCM and at -78 C, a solution of DMSO (17.1 mL, 0.241 mol) in DCM (25 mL) was added dropwisely. After 30 min, benzyl 4- (hydroxymethyl)-piperidine-l-carboxylate (20 g, 0.080 mol) in DCM (25 mL) was added dropwisely. After 30 min, Et3N (44.7 mL, 0.321 mol) was added. The resulting solution was stirred for 30 min at -78 C. The reaction was diluted with water, extracted with DCM (3 x). Combined organic layers were washed with water (3 x 500 mL), dried over Na2S04, filtered and concentrated to give Intermediate 6C (18.5 g, 93.0%). MS (ESI) m/z 247 (M+H)+.

122860-33-7, The synthetic route of 122860-33-7 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; BRISTOL-MYERS SQUIBB COMPANY; THIBEAULT, Carl; CLARK, Charles, G.; DELUCCA, Indawati; HU, Carol, Hui; JEON, Yoon; LAM, Patrick, Y., S.; QIAO, Jennifer, X.; YANG, Wu; WANG, Yufeng; WANG, Tammy, C.; WO2014/22349; (2014); A1;,
Piperidine – Wikipedia
Piperidine | C5H11N – PubChem