Triethylamine → N-(1-methyl-1H-indol-3-ylmethyl)-N-methylacrylamide

HRID 18322Notes

Reaction equation

HRID 18322 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([CH2:11][NH:12][CH3:13])=[CH:3]1.CCN(CC)CC.[C:21](Cl)(=[O:24])[CH:22]=[CH2:23]>C(Cl)Cl>[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([CH2:11][N:12]([CH3:13])[C:21](=[O:24])[CH:22]=[CH2:23])=[CH:3]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 13140Acryloyl chlorideHCID 109867781-Methyl-3-(methylaminomethyl)indole

Product 1

HCID 22139011N-(1-methyl-1H-indol-3-ylmethyl)-N-methylacrylamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 1-methyl-3-(methylaminomethyl)-1H-indole (1.0 g, 5.7 mmole) and Et3N (0.8 mL, 5.7 mmole) in CH2Cl2 (50 mL) at 0° C. was added acryloyl chloride (0.47 mL, 5.8 mmole) in one portion. After stirring for 1 h the reaction was washed with cold H2O and brine, then was dried (MgSO4) and concentrated under vacuum. This material was used without further purification.

Workup

  1. washwas washed with cold H2O and brine
  2. dry with materialwas dried (MgSO4)
  3. concentrationconcentrated under vacuum
  4. customThis material was used without further purification

Sources & evidence

ORD record
ord-78fc11590cd44f0589c776fe8ebc69b8
Source dataset
uspto-grants-2010_06
Patent number
US07741339B2

Reaction notes

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