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

HRID 324630

Reaction equation

HRID 324630 reaction equation
[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]

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-a366750548a9491ea8a8b9742f811e8f
Source dataset
uspto-grants-2001_04
Patent number
US06218429B1

Linked notes

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