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

HRID 324630

反応式

HRID 324630 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
50 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-a366750548a9491ea8a8b9742f811e8f
出典データセット
uspto-grants-2001_04
特許番号
US06218429B1

関連ノート

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