Cornforth reagent → 1-[1-(3,4-Dichlorobenzyl)piperidin-4-yl]-3-methyl-2-butanone

HRID 430698노트

반응식

HRID 430698 반응식
[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=O.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.[Cl:22][C:23]1[CH:24]=[C:25]([CH:39]=[CH:40][C:41]=1[Cl:42])[CH2:26][N:27]1[CH2:32][CH2:31][CH:30]([CH2:33][CH:34]([OH:38])[CH:35]([CH3:37])[CH3:36])[CH2:29][CH2:28]1>CN(C)C=O>[Cl:22][C:23]1[CH:24]=[C:25]([CH:39]=[CH:40][C:41]=1[Cl:42])[CH2:26][N:27]1[CH2:32][CH2:31][CH:30]([CH2:33][C:34](=[O:38])[CH:35]([CH3:37])[CH3:36])[CH2:29][CH2:28]1

참가 물질

4

반응물 2

HCID 2724130Cornforth reagentHCID 222576701(RS)-[1-(3,4-dichlorobenzyl)piperidin-4-ylmethyl]-2-methylpropanol

생성물 1

HCID 222577801-[1-(3,4-Dichlorobenzyl)piperidin-4-yl]-3-methyl-2-butanone수율 65%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
0 °C

실험 절차

Pyridinium dichromate (4.0 g, 10.63 mmol) was added to a solution of 1(RS)-[1-(3,4-dichlorobenzyl)piperidin-4-ylmethyl]-2-methylpropanol (0.5 g, 1.5 mmol) in dimethylformamide (25 ml) at 0° C. The resulting solution was stirred at 0° C. until the starting material was consumed and then quenched with water, basified with 2N sodium hydroxide and extracted with ethyl acetate. The organic layer was washed with water, brine, and dried over sodium sulfate. The residue was purified on silica gel with 25% acetone, 25% dichloromethane in hexanes to give 1-[1-(3,4-dichlorobenzyl)piperidin-4-yl]-3-methyl-2-butanone (0.32 g) as an oil.

후처리

  1. customwas consumed
  2. customquenched with water
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with water, brine
  5. dry with materialdried over sodium sulfate
  6. customThe residue was purified on silica gel with 25% acetone, 25% dichloromethane in hexanes

출처 및 근거

ORD 기록
ord-ce08f1ae08044d6d82abb4f682cf727d
출처 데이터셋
uspto-grants-2001_11
특허 번호
US06323223B1

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