Dimethyl Sulfoxide → 1-(4-Methylbenzyl)piperidin-4-one

HRID 49443

반응식

HRID 49443 반응식
C(Cl)(=O)C(Cl)=O.CS(C)=O.[CH3:11][C:12]1[CH:25]=[CH:24][C:15]([CH2:16][N:17]2[CH2:22][CH2:21][CH:20]([OH:23])[CH2:19][CH2:18]2)=[CH:14][CH:13]=1.C(N(CC)CC)C.[Cl-].[NH4+]>C(Cl)Cl>[CH3:11][C:12]1[CH:13]=[CH:14][C:15]([CH2:16][N:17]2[CH2:18][CH2:19][C:20](=[O:23])[CH2:21][CH2:22]2)=[CH:24][CH:25]=1

참가 물질

7

반응물 5

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 65578Oxalyl chlorideHCID 7914821-(4-Methylbenzyl)piperidin-4-ol

생성물 1

HCID 119595411-(4-Methylbenzyl)piperidin-4-one수율 81%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

To 2.8 mL (32 mmol) of oxalyl chloride in 75 mL of CH2Cl2 at −78° C. was added 4.6 mL (64 mmol) of DMSO. To this mixture was added 5.3 g (26 mmol) of 1-(4-methylbenzyl)-4-piperidinol 123 in 10 mL of CH2Cl2, and the mixture was stirred 5 min in the cold. The mixture was quenched with 18 mL (129 mmol) of triethylamine and allowed to come to room temperature, and saturated aqueous ammonium chloride was added. The organic phase was washed with water and brine, dried, and evaporated to give 4.27 g (81%) of 1-(4-methylbenzyl)-4-piperidinone (124), which was used as is without further purification. GC/MS showed 100% purity with a molecular ion of 203.

후처리

  1. customto come to room temperature
  2. washThe organic phase was washed with water and brine
  3. customdried
  4. customevaporated

출처 및 근거

ORD 기록
ord-fb7270a74cbc4031b8e83c2f70138da2
출처 데이터셋
uspto-grants-2004_03
특허 번호
US06706740B2

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