Category: 19099-93-5

19099-93-5, 1-Cbz-Piperidin-4-one is a piperidines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

[32.2] To a stirred solution of the product (130 g) obtained in preparation 1 in methanol (500 ml) at 0C., sodium borohydride (25 g) was added and the reaction mixture was stirred at the same temperature for 1h. At the end of this time, pH was adjusted to 6.5 – 7.0 using AcOH and the solvent was removed under reduced pressure. The residue was diluted with EtOAc (400 ml) was washed with water, dried (Na2SO4) and the solvent was removed under reduced pressure to get 131 g (100%) of the title compound as a syrupy liquid. 1H NMR (CDCl3, 200MHz): d 1.5 (m,2H), 1.85 (m.2H), 3.15 (m,2H), 3.9 (m, 3H), 5.11 (s, 2H), 7.35 (bs, 5H).

19099-93-5, 19099-93-5 1-Cbz-Piperidin-4-one 643496, apiperidines compound, is more and more widely used in various fields.

Reference：
Patent; Dr. Reddy’s Laboratories Ltd.; EP981526; (2004); B1;,
Piperidine – Wikipedia
Piperidine | C5H11N – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.19099-93-5,1-Cbz-Piperidin-4-one,as a common compound, the synthetic route is as follows.

Benzyl 4-oxopiperidine-l-carboxylate (5g, 21 mmol) in THF (50 ml) was cooled to 0C. Sodium hydride (1.1 g, 43 mmol), then iodomethane (3.0 ml, 47 mmol) was added slowly. Mixture was stirred at 0C for 2 hours, then slowly warm up to room temperature and stirred overnight. Saturated aq. NH4C1 solution was added and the product was extracted with EtOAc. The extract was washed with brine, dried over anhydrous sodium sulfate, and concentrated. The crude product thus obtained was purified by column chromatography on a 100 gram-size silica gel column, eluting with gradient EtOAc/hexane to afford the titled product as colorless oil.

19099-93-5, The synthetic route of 19099-93-5 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; MERCK SHARP & DOHME CORP.; ALI, Amjad; LO, Michael Man-Chu; LIM, Yeon-Hee; STAMFORD, Andrew; KUANG, Rongze; TEMPEST, Paul; YU, Younong; HUANG, Xianhai; HENDERSON, Timothy J.; KIM, Jae-Hun; BOYCE, Christopher; TING, Pauline; ZHENG, Junying; METZGER, Edward; ZORN, Nicolas; XIAO, Dong; GALLO, Gioconda V.; WON, Walter; WU, Heping; WO2014/101373; (2014); A1;,
Piperidine – Wikipedia
Piperidine | C5H11N – PubChem

19099-93-5, 1-Cbz-Piperidin-4-one is a piperidines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

490 g of ammonium carbonate and 70 g of potassium cyanide were added to the reaction flask,700 mL of water and 700 mL of ethanol were added. Finally, 100 g of 1-benzyloxycarbonyl-4-piperidone was added, heated to 60 C, and reacted till the inorganic salt dissolves completely. After a period of time there will be a lot of crystals appear, reacted for 24 hours, and cooled to room temperature. The reaction solution was filtered off and the cake was washed with 1000 mL of water. The filter cake was then added to a 2000 mL mixture of ethanol and water (V ethanol: V = 4: 1), heated to 50C after slow cooling, followed by recrystallization to give 130 g of compound 5.

19099-93-5, The synthetic route of 19099-93-5 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; Henan Normal University; Mao Longfei; Jia Shuhong; Li Wei; Wu Doucan; Dong Wenpei; Shen Jiaxuan; Jiang Tao; Xu Guiqing; Jiang Yuqin; (9 pag.)CN105017252; (2017); B;,
Piperidine – Wikipedia
Piperidine | C5H11N – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.19099-93-5,1-Cbz-Piperidin-4-one,as a common compound, the synthetic route is as follows.

To a -20 0C solution of N,N,N’,N’-tetraniethylethylenediamine (0.335 g, 2.89 mmol) in THF (1 mL) was added n-butyllithium (2.5M, 1.15 mL, 2.89 mmol) over 10 min. After 30 min, the mixture was cooled to -78 0C and tert-butyl (6-chloropyridin-2-yl)carbamate (0.300 g, 1.31 mmol) in THF (0.8 mL) was added over 15 min. After Ih, the reaction was warmed to -50 0C, stirred for 2h and then N-benxyloxycarbonyl-4-piperidinone (0.459 g, 1.97 mmol) in THF (1 mL) was added over 10 min. The reaction was allowed to warm to room temperature and then stirred for 24 h. A solution of saturated aqueous NaHCO3 was added and the mixture extracted with EtOAc (3x). The combined organic layers were washed with H2O, brine, dried over MgStheta4, filtered, and concentrated under reduced pressure. The crude product was purified by silica gel chromatography, eluting with a gradient of 25 to 50% ethyl acetate: hexane to give the title compound (0.160 g). MS: mlz = 338.0 (M + 1).

19099-93-5, 19099-93-5 1-Cbz-Piperidin-4-one 643496, apiperidines compound, is more and more widely used in various fields.

Reference：
Patent; MERCK & CO., INC.; WO2006/99268; (2006); A2;,
Piperidine – Wikipedia
Piperidine | C5H11N – PubChem

19099-93-5, 1-Cbz-Piperidin-4-one is a piperidines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

At 0C, to a solution of benzyl 4-oxopiperidine-1-carboxylate (2.00 g, 8.57 mmol, 1.00 equivalent) in tetrahydrofuran(25 mL) were added sodium hydride (719.88 mg, 18.00 mmol, 2.10 equivalents) and potassium iodide (3.80g, 26.74 mmol, 3.12 equivalents) in one portion. The mixture was stirred at 30C for 16 hours. LC/MS showed completionof the reaction. The reaction mixture was added a solution of ammonium chloride (50 mL) thereto and then subjectedto extraction using ethyl acetate (50 mL32). The organic phase was concentrated and dried. The obtained residue waspurified by preparative TLC plate (petroleum ether: ethyl acetate = 6: 1) to give the title compound (870.00 mg, 3.33mmol, 38.86% yield) as a transparent oil. 1H NMR (400 MHz, Methanol-d4) delta 7.38-7.33 (m, 5H), 5.19 (s, 2H), 3.81-3.77(t, J = 6.4 Hz, 2H), 3.50-3.46 (m, 2H), 2.50 (s, 2H), 1.11-1.04 (m, 6H). LC/MS (ESI) m/z: 284.1 (M+1).

19099-93-5, The synthetic route of 19099-93-5 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; Chai Tai Tianqing Pharmaceutical Group Co., Ltd.; Medshine Discovery Inc.; DING, Charles Z.; CHEN, Shuhui; ZHAO, Baoping; XU, Zhaobing; LIU, Yingchun; LIN, Ruibin; WANG, Fei; LI, Jian; (101 pag.)EP3269715; (2018); A1;,
Piperidine – Wikipedia
Piperidine | C5H11N – PubChem

19099-93-5, 1-Cbz-Piperidin-4-one is a piperidines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Step 2: benzyl 7′-chloro-2′-oxo-1′,2′-dihydrospiro[piperidine-4,4′-pyrido[2,3d]-[1,3]oxazine]-1-carboxylate Under a nitrogen atmosphere 26 mL (173.39 mmol) N,N,N,N-tetramethylenethylene-diamine in 180 mL THF were cooled to -20 C. and within 10 min 70 mL (175 mmol) of a 2.5 molar butyllithium solution were added. After 30 minutes’ stirring the reaction mixture was cooled to -78 C. and at this temperature 17.84 g (78.00 mmol) tert-butyl (6-chloro-pyridin-2-yl)-carbamate in 120 mL THF were added dropwise within 20 min. The reaction mixture was stirred for 2.5 h at -78 C. and then combined with 27.22 g (116.70 mmol) Z-piperidone in 60 mL THF within 10 min. After a further hour’s stirring at -78 C. the reaction mixture was first of all heated to RT and then stirred for 18 h at 40 C. Then the reaction mixture was decomposed by the dropwise addition of 150 mL saturated sodium hydrogen carbonate solution. Then the reaction mixture was extracted several times extracted with DCM. The combined organic phases were washed with water, dried and evaporated down. The residue was triturated with PE/EtOAc 1/1, the precipitate formed was suction filtered, washed with PE/ETOAc 1/1 and dried.Yield: 16.40 g (54% of theoretical)ESI-MS: m/z=388 (M+H)+ Rt(HPLC): 1.57 min (method C), 19099-93-5

19099-93-5 1-Cbz-Piperidin-4-one 643496, apiperidines compound, is more and more widely used in various fields.

Reference：
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; US2012/149698; (2012); A1;,
Piperidine – Wikipedia
Piperidine | C5H11N – PubChem

19099-93-5, 1-Cbz-Piperidin-4-one is a piperidines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

n-Butyllithium is added dropwise to a solution at -20 C. of N,N,N’,N’-tetramethylethylenediamine in tetrahydrofuran. After stirring for thirty minutes, the mixture is cooled to -78 C. and a solution of (6-chloro-pyridin-2-yl)-tert-butyl carbamate in tetrahydrofuran is added. The reaction is maintained at -50 C. for two hours and then a solution of 4-oxo-piperidine-1-benzyl carboxylate in tetrahydrofuran is added dropwise. The reaction mixture is brought back to room temperature slowly and then heated at 40 C. for 18 hours. The reaction mixture is hydrolysed with a saturated aqueous solution of sodium hydrogen carbonate and then diluted with dichloromethane. The product is extracted with dichloromethane, the organic phases are combined, washed once with water and then dried over magnesium sulphate, filtered and concentrated under vacuum. The crude product is chromatographed on silica gel eluted with a heptane/ethyl acetate mixture, 70/30 and then 50/50. 7′-chloro-2′-oxo-1′,2′-dihydro-1H-spiro[piperidine-4,4′-pyrido[2,3-d][1,3]oxazine]-1-benzyl carboxylate is obtained in the form of a yellow solid.

19099-93-5, As the paragraph descriping shows that 19099-93-5 is playing an increasingly important role.

Reference：
Patent; GALDERMA RESEARCH & DEVELOPMENT; Fournier, Jean-Francois; Clary, Laurence; Thoreau, Etienne; (164 pag.)US2018/50992; (2018); A1;,
Piperidine – Wikipedia
Piperidine | C5H11N – PubChem

19099-93-5, 1-Cbz-Piperidin-4-one is a piperidines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Step 2: benzyl 7′-chloro-2′-oxo-1′,2′-dihydrospiro[piperidine-4,4′-pyrido[2,3d][1,3]-oxazin]-1-carboxylate Under a nitrogen atmosphere 26 mL (1734 mmol) N,N,N,N-tetramethylenethylenediamine in 180 mL THF were cooled to -20 C. and 70 mL (175 mmol) of a 2.5 molar butyllithium solution were added within 10 min. After 30 minutes’ stirring the reaction mixture was cooled to -78 C. and at this temperature 17.8 g (78.0 mmol) tert-butyl (6-chloro-pyridin-2-yl)-carbamate in 120 mL THF were added dropwise within 20 min. The reaction mixture was stirred for 2.5 h at -78 C. and then 27.2 g (116.7 mmol) benzyl 4-oxo-piperidine-1-carboxylate in 60 mL THF were added within 10 min. After another hour’s stirring at -78 C. the reaction mixture was first of all heated to RT and then stirred for 18 h at 40 C. Then the reaction mixture was decomposed by the dropwise addition of 150 mL saturated sodium hydrogen carbonate solution. Then the reaction mixture was extracted several times with DCM. The combined organic phases were washed with water, dried and evaporated down. The residue was triturated with PE/EtOAc 1/1, the precipitate formed was suction filtered, washed with PE/ETOAc 1/1 and dried. Yield: 16.4 g (54% of theoretical) ESI-MS: m/z=388 (M+H)+ Rt(HPLC): 1.57 min (method C)

19099-93-5, As the paragraph descriping shows that 19099-93-5 is playing an increasingly important role.

Reference：
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; US2011/21500; (2011); 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.19099-93-5,1-Cbz-Piperidin-4-one,as a common compound, the synthetic route is as follows.

To a stirred solution of benzyl 4-oxopiperidine-l-carboxylate (2.37 g, 10.17 mmol) in EtOH (50 mL) at 0 0C under a nitrogen atmosphere was added NaBH4 (0.42 g, 11.19 mmol) in one portion. The reaction mixture was warmed to RT and stirred for 2 h. The resulting reaction mixture was cooled to O0C and aqueous ammonium chloride (20 mL) added. The solvent was evaporated at reduced pressure, aqueous phase extracted with DCM (3 x 20 mL), organics separated, combined, dried (MgSO4), filtered and concentrated to give colourless oil (2.39 g, 100 % yield). The title compound was used without further purification. LCMS data: Calculated MH+ (236.29); Found 66% (MH+) m/z 236.21, Rt = 3.69 min. 1H NMR (250 MHz, CHLOROFORM-J) delta ppm 7.29 – 7.58 (5 H, m), 5.13 (2 H, s), 3.77 – 4.10 (3 H, m), 3.02 – 3.30 (2 H, m), 1.73 – 1.98 (2 H, m), 1.39 – 1.69 (3 H, m)., 19099-93-5

As the paragraph descriping shows that 19099-93-5 is playing an increasingly important role.

Reference：
Patent; EVOTEC NEUROSCIENCES GMBH; WO2009/121812; (2009); 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.19099-93-5,1-Cbz-Piperidin-4-one,as a common compound, the synthetic route is as follows.

Step A: Benzyl 3,3-dimethyl-4-oxopiperidine-l -carboxylate [0214] Benzyl 4-oxopiperidine-l-carboxylate (5g, 21 mmol) in THF (50 ml) was cooled to 0 C. Sodium hydride (1.1 g, 43 mmol), then iodomethane (3.0 ml, 47 mmol) was added slowly. Mixture was stirred at 0 C for 2 hours, then slowly warm up to room temperature and stirred overnight. Saturated aq. NC1 solution was added and the product was extracted with EtOAc. The extract was washed with brine, dried over anhydrous sodium sulfate, and concentrated. The crude product thus obtained was purified by column chromatography on a 100 gram-size silica gel column, eluting with gradient EtOAc/hexane to afford the titled product as colorless oil.

19099-93-5, 19099-93-5 1-Cbz-Piperidin-4-one 643496, apiperidines compound, is more and more widely used in various fields.

Reference：
Patent; MERCK SHARP & DOHME CORP.; ALI, Amjad; LO, Michael; LIM, Yeon Hee; STAMFORD, Andrew; KUANG, Rongze; TEMPEST, Paul; YU, Younong; HUANG, Xianhai; HENDERSON, Timothy J.; KIM, Jae-Hun; BOYCE, Christopher; TING, Pauline; ZHENG, Junying; METZGER, Edward; ZORN, Nicolas; XIAO, Dong; GALLO, Gioconda; WON, Walter; WU, Heping; WO2014/101120; (2014); A1;,
Piperidine – Wikipedia
Piperidine | C5H11N – PubChem