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

HRID 584719

反応式

HRID 584719 の反応式
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

参加物

7

反応物 5

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

生成物 1

HCID 119595411-(4-Methylbenzyl)piperidin-4-one収率 81%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-8cff7da1787b4f3389584bbc8a1b0715
出典データセット
uspto-grants-2005_08
特許番号
US06927225B2

関連ノート

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