Category: 3612-20-2

3612-20-2, 1-Benzylpiperidin-4-one is a piperidines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Exemplary Procedure for the Synthesis of Spiro-piperidine Hydantoin Scaffold for R1 Analogs. As depicted in Scheme 7 above, N-benzyl-4-piperidone (20 g, 106 mmol), NaCN (7.9 g, 160.4 mmol), and (NH4)2CO3 (52 g, 542 mmol) in EtOH (50 mL) and H2O (50 mL) was heated at 60 C. overnight. Upon cooling to ambient temperature, the white solid was filtered, washed with warm H2O, and dried in vacuo to provide 27.4 g. The solid (3.0 g, 11.6 mmol) was dissolved in DMF (30 mL), NaH (0.51 g of 60% dispersion in mineral oil, 12.8 mmol) was added, stirred at ambient temperature 2 hours, then 3-methoxybenzyl bromide (11.6 mmol) was added and the reaction was stirred overnight. Typical aqueous work-up provided 5.5 g ER-811159 as a solid which could be recrystallized from MeOH.Alternative Procedure for the Synthesis of Spiro-piperidine Hydantoin Scaffold for R1 Analogs. As depicted in Scheme 8 above, N-benzyl-4-piperidone (20 g, 106 mmol), NaCN (7.9 g, 160.4 mmol), and (NH4)2CO3 (52 g, 542 mmol) in EtOH (50 mL) and H2O (50 mL) was heated at 60 C. overnight. Upon cooling to ambient temperature, the white solid was filtered, washed with warm H2O, and dried in vacuo to provide 27.4 g. The solid (3.5 g, 13.3 mmol), 3-methoxybenzyl bromide (13.3 mmol), and DBU (20 mmol) were dissolved in NMP (30 mL), separated into 5 vials and each vial was microwave heated at 180 C. for 60 s. The batches were combined, subjected to typical aqueous work-up, then recrystallized from MeOH/MTBE/hexanes to provided 2.2 g ER-811159.

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

Reference：
Patent; Gallagher, Brian M.; Carlson, Eric; Chen, Qian; Davis, Heather; Schiller, Shawn; Shaffer, Christina; Spyvee, Mark; Wong, Nancy; US2006/270696; (2006); A1;,
Piperidine – Wikipedia
Piperidine | C5H11N – PubChem

3612-20-2, 1-Benzylpiperidin-4-one is a piperidines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Intermediate F: 9-benzyl-4-oxa-1 ,9-diazaspiro[5.5]undecan-2-one Step 1 : 8-benzyl-1 ,3,8-triazaspiro[4.5]decane-2,4-dione: 1-Benzyl-4-piperidone (10 g, 52.8 mmol) was added to a suspension of sodium cyanide (7 g, 143 mmol) and ammonium bicarbonate (40.2 g, 508 mmol) in a mixture of ethanol (70 mL) and water (70 mL). The resulting mixture was stirred at 60 C for 36 h. The solids were collected by filtration, washed with warm water (2x 20 mL) and dried under vacuum to yield 20.6 g of a crude product that was slurried in a mixture of of ethanol (240 mL) and water (60 mL). The solids were collected by filtration and dried under vacuum to yield the title compound (16 g, 13.7 g theoretical weight; quant yield). HPLC retention time (method A): 2.46 min; MS: 260.1 (M+H)., 3612-20-2

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

Reference：
Patent; LABORATORIOS DEL DR. ESTEVE, S.A.; VIRGILI-BERNADO, Marina; ALEGRET-MOLINA, Carlos; ALMANSA-ROSALES, Carmen; (177 pag.)WO2016/78771; (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.3612-20-2,1-Benzylpiperidin-4-one,as a common compound, the synthetic route is as follows.

To a solution of ammonium chloride (5.7 g, 105.6 mmol) and potassium cyanide (6.9 mg, 105.6 mmol) in water (155 mL) was added 1-benzyl-4-piperidone (5 g, 26.4 mmol) and the mixture was stirred for 6 days. It was cooled to 0 C. and pH was adjusted to 11 by adding K2CO3. The reaction mixture was extracted with ethyl acetate three times. The combined organic layer was dried over MgSO4, filtered and evaporated to give the oil (5 g), which was a mixture of the desired aminonitrile, cyanohydrin and starting ketone. The crude mixture was used in next step without further purification. 1H NMR (400 MHz, CDCl3) delta 7.36-7.25 (m, 5H), 2.77-2.74 (m, 2H), 2.48-2.31 (m, 4H), 2.13-2.08 (m, 2H), 1.81-1.74 (m, 2H).

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

Reference：
Patent; Cumbre Inc.; US2005/277633; (2005); 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.3612-20-2,1-Benzylpiperidin-4-one,as a common compound, the synthetic route is as follows.

8-benzyl-1,3,8-triazaspiro[4.5]decane-2,4-dione1-Benzylpiperidin-4-one (49A) (20.0 g, 105.68 mmol)Soluble in ethanol (140mL), add potassium cyanide with stirring(14.3 g, 219.6 mmol) and water (140 mL),The mixture was stirred at 85 C for 36 hours.The reaction solution was cooled to room temperature, filtered, and the filter cake was washed with hot water (100 mL×3).The filter cake is dried to a white solid8-benzyl-1,3,8-triazaspiro[4.5]decane-2,4-dione (49B)(24.3 g, yield: 88.68%)., 3612-20-2

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

Reference：
Patent; Sichuan Hai Sike Pharmaceutical Co., Ltd.; Fan Jiang; Zhu Fengfei; Chen Qingping; Wang Chengtao; (251 pag.)CN109206417; (2019); 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.3612-20-2,1-Benzylpiperidin-4-one,as a common compound, the synthetic route is as follows.

STEP A: 4-Amino-1-benzylpiperidine-4-carbonitrile To a solution of ammonium chloride (17.3 g, 323 mmol) in water (200 mL) was added successively aqueous 25% ammonia (25 mL, 332 mmol) and 1-benzylpiperidin-4-one (11.43 g, 60 mmol). The resulting mixture was stirred at room temperature for 20 min and sodium cyanide (14.7 g, 300 mmol) was added in portions over 15 min. After stirring for 1 day, the reaction mixture was partitioned between water (200 mL) and DCM (2*200 mL). The organic phase was dried over MgSO4, filtered and concentrated in vacuo to yield a residue. The residue was purified by flash chromatography (silica gel, 50% EtOAc/heptanes to 100% EtOAc) to yield 4-amino-1-benzylpiperidine-4-carbonitrile (6.15 g, 47%). 1H NMR (300 MHz, CDCl3) delta ppm 1.69-1.86 (m, 4H), 2.00 (dt, J=13.1, 2.1 Hz, 2H), 2.27-2.45 (m, 2H), 2.83 (dt, J=12.4, 3.6 Hz, 2H), 3.55 (s, 2H), 7.21-7.39 (m, 5H); MS m/z 216 (M+H)+.

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

Reference：
Patent; Janssen Pharmaceutica, NV; Connolly, Peter J.; US2015/99730; (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.3612-20-2,1-Benzylpiperidin-4-one,as a common compound, the synthetic route is as follows.

(a) Synthesis of 1-benzylpiperidine-4-carbaldehyde To a solution of diisopropylamine (14.8 ml, 106 mmol) in tetrahydrofuran (20 ml) was added dropwise 1.59M-n-butyllithium (7.9 ml, 12.7 mmol) at -78C over a period of 10 minutes, and stirred for 30 minutes. Then, 2M-trimethylsilyldiazomethane (6.34 ml, 12.7 mmol) was added dropwise thereto at -78C over a period of 5 minutes and stirred for 30 minutes. Thereafter, a solution of 1-benzyl-4-piperidone (2.0 g, 10.6 mmol) in tetrahydrofuran (20 ml) was added dropwise thereto at -78C over a period of 30 minutes, and the resulting mixture was stirred at -78C for 1 hour, warmed up to room temperature, stirred for 30 minutes and then refluxed for 2 hours. After completion of the reaction, the reaction mixture was poured onto ice and extracted with ethyl acetate. The organic layer was dried over magnesium sulfate and distilled under reduced pressure to remove the solvent, and to a solution of the resulting residue in ethyl acetate (200 ml) was added silica gel (10 g) at room temperature, and stirred overnight. Then, the solvent was distilled off and the resulting residue was purified by a silica gel column chromatography (eluent: chloroform/methanol = 50/1) to obtain 1-benzylpiperidine-4-carbaldehyde (1.19 g, 55%)., 3612-20-2

The synthetic route of 3612-20-2 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; Sumitomo Pharmaceuticals Company, Limited; EP1500643; (2005); 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.3612-20-2,1-Benzylpiperidin-4-one,as a common compound, the synthetic route is as follows.

To a mixture of N-benzylpiperidin-4-one 1 (0.01 mol, 1.89 g), aniline (0.01 mol), and activated zinc (0.04 mol), 90% aqueous acetic acid (0.16 mol) was added in portions. The mixture was stirred at room temperature for 24 h and at 70C on a water bath for an additional 12 h. After the reaction completion, the mixture was diluted with methanol and filtered. The filtrate was concentrated in a vacuum and then neutralized with a 30% ammonium hydroxide solution to pH 10. The crude product was collected by filtration and recrystallized with petroleum ether to obtain the pure product in 84% yield (2.2 g). IR (KBr), nu, cm-1: 3440 (N-H stretching), 3255, 3020, 2936, 2842,1615, 1526, 1490, 1372, 1318,1255, 1087, 977, 862, 751, 690. 1H NMR [400 MHz,CDCl3, delta (ppm)]: 1.50 (dq, 2H), 2.10 (br.d, 2H), 2.30(br.t, 2H), 2.60 (s, 2H), 2.90 (br.d, 2H), 3.35 (m, 1H),3.50 (br.s, 1H), 7.10-7.40 (m, Ar-H). Mass spectrum(m/z): 267 [M + 1]., 3612-20-2

The synthetic route of 3612-20-2 has been constantly updated, and we look forward to future research findings.

Reference：
Article; Nami; Dabiri; Shirvani; Ahmadi Faghih; Javaheri; Radiochemistry; vol. 60; 1; (2018); p. 42 – 44; Radiokhimiya; vol. 60; 1; (2018); p. 42 – 44,4;,
Piperidine – Wikipedia
Piperidine | C5H11N – PubChem

3612-20-2, 1-Benzylpiperidin-4-one is a piperidines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Step 1 Sodium triacetoxyhydroborate (1.1 g, 5.3 mmol) was added to a solution of 1-benzyl-4-piperidone (1.0 g, 5.3 mmol) and aniline (0.5 g, 5.3 mmol) in a mixture of chloroform/ethyl acetate (10 mL/5 mL) by portions, and the mixture was stirred at room temperature for 40 minutes. To the reaction mixture was added an aqueous saturated sodium bicarbonate solution (50 ml), the mixture was extracted with ethyl acetate (3×50 ml), the organic layer was dried over anhydrous magnesium sulfate, and the solvent was distilled off. The residue was purified by silica gel column chromatography (solvent: hexane-ethyl acetate) to obtain (1-benzyl-4-piperidinyl)phenylamine (0.9 g, 64%). 1H-NMR (CDCl3) delta: 1.49 (2H, m), 2.04 (2H, m), 2.17 (2H, dt, J = 2.3 Hz, 10.8 Hz), 2.86 (2H, br d, J = 12.0 Hz), 3.30 (1H, m), 3.54 (2H, s), 6.50-7.35 (10H, m)., 3612-20-2

3612-20-2 1-Benzylpiperidin-4-one 19220, apiperidines compound, is more and more widely used in various fields.

Reference：
Patent; Takeda Pharmaceutical Company Limited; EP1559428; (2005); A1;,
Piperidine – Wikipedia
Piperidine | C5H11N – PubChem

3612-20-2, 1-Benzylpiperidin-4-one is a piperidines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

1 -Benzyl-4-piperidone (1.89 g, 10 mmol) was dissolved in 15 ml acetone. Methyliodide (0.90 ml, 15 mmol) was slowly added over 5 min. After 2 hrs magnetic stirring additional Methyliodide (1.8 ml, 30 mmol) was added. After 1 hr magnetic stirring 20 ml diethyl-ether was added. Crude product was collected by filtration and washed with acetone/diethyl ether. White crystals were dried under vacuum giving 806 mg quartenary salt. TLC (10% methanol in dichloromethane): Rf =0.7. Partly dissolved salt in 5 ml water was added to 50 C. hot mixture of t-Butylamine (120 mg, 1.6 mmol) and Potassiumcarbonate (32 mg, 0.22 mmol) in 3 ml ethanol. The resulting mixture was stirred and heated to reflux (~80 C.) for 1 hr. After cooling water (20 ml) and dichloromethane (20 ml) were added. Phases were separated and aq. phase was re- extracted with dichloromethane and ethylacetate. Combined organic phases were dried over MgSO4 and concentrated on Rotavapor (40 C.) giving 496 mg 47AKU-47. TLC (10% methanol in dichloromethane): Rf=0.3. 1H-NMR (400 MHz, CDCl3): delta 2.82 (4H31); 2.41 (4H5 t); 1.12 (9H, s). 13C-NMR (CDCl3): delta 210.2, 54.3, 46.4, 42.4, 26.6. Crude product contained ~25% (1H-NMR) starting material (l-Benzyl-4-piperidone)., 3612-20-2

The synthetic route of 3612-20-2 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; ACADIA PHARMACEUTICALS, INC.; WO2007/124136; (2007); A1;,
Piperidine – Wikipedia
Piperidine | C5H11N – PubChem

3612-20-2, 1-Benzylpiperidin-4-one is a piperidines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Step A 1-benzyl-4-(methylamino)piperidine A solution of 1 mol of N-benzylpiperid-4-one in 2200 cm3 of isopropanol is cooled to 18 C. A freshly prepared solution of 3 mol of methylamine in 300 cm3 of methanol is added to the first solution. The mixture is left at that temperature for one hour. 1.66 mol of sodium hydroxide in the form of pellets are added. 1.37 mol of sodium borohydride are added at a constant temperature of 18 C. The mixture is allowed to return to room temperature and then the reagents are left in contact for 12 hours. The solvents are evaporated, and the residue is taken up in ether and then washed with water. Drying and evaporation yield an oil which is the desired compound. Yield: 78%., 3612-20-2

3612-20-2 1-Benzylpiperidin-4-one 19220, apiperidines compound, is more and more widely used in various fields.

Reference：
Patent; Adir et Compagnie; US5298503; (1994); A;,
Piperidine – Wikipedia
Piperidine | C5H11N – PubChem