Dimethylformamide → N-[2-(5-allyloxyindol-3-yl)ethyl]propionamide

HRID 1636603

반응식

HRID 1636603 반응식
[CH2:1](Br)[CH:2]=[CH2:3].[OH:5][C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[NH:11][CH:10]=[C:9]2[CH2:15][CH2:16][NH:17][C:18](=[O:21])[CH2:19][CH3:20].C(=O)([O-])[O-].[Cs+].[Cs+].CN(C)C=O>O>[CH2:1]([O:5][C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[NH:11][CH:10]=[C:9]2[CH2:15][CH2:16][NH:17][C:18](=[O:21])[CH2:19][CH3:20])[CH:2]=[CH2:3]

참가 물질

6

반응물 4

HCID 6228DimethylformamideHCID 7841Allyl bromideHCID 10796Cesium carbonateHCID 594440N-Propionylserotonin

생성물 1

HCID 22004842N-[2-(5-allyloxyindol-3-yl)ethyl]propionamide수율 80.9%

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
50 °C

실험 절차

Allyl bromide (11 g, 90.8 mmol.) was added, under argon atmosphere, to a mixture of N-[2-(5-hydroxyindol-3-yl)ethyl]propionamide (20.0 g, 92.5 mmol.), cesium carbonate (31.6 g, 97 mmol.) and N,N-dimethylformamide (150 mL) at 0° C. The reaction mixture was stirred for one hour at 50° C., to which was added water. The product was extracted with ethyl acetate. The extract solution was washed with water and dried. The solvent was then distilled off to leave the title compound (yield 20.0 g, 79.4%) as an oily product. This product was used, without further purification, for the subsequent reaction.

후처리

  1. extractionThe product was extracted with ethyl acetate
  2. washThe extract solution was washed with water
  3. customdried
  4. distillationThe solvent was then distilled off

출처 및 근거

ORD 기록
ord-67fca0d80f674679a540f033bd6de4f6
출처 데이터셋
uspto-grants-2000_03
특허 번호
US06034239

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