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

HRID 1690317Notes

Reaction equation

HRID 1690317 reaction equation
[C:1](Cl)(=[O:4])[CH:2]=[CH2:3].[CH3:6][NH:7][CH2:8][C:9]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[NH:11][CH:10]=1.CCN(CC)CC>C(Cl)Cl>[NH:11]1[C:12]2[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:9]([CH2:8][N:7]([CH3:6])[C:1](=[O:4])[CH:2]=[CH2:3])=[CH:10]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 13140Acryloyl chlorideHCID 96388N-Methyl-1H-indole-3-methanamine

Product 1

HCID 22139147N-(1H-indol-3-ylmethyl)-N-methylacrylamideYield 80.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Acryloyl chloride (0.33 mL, 4.10 mmole) was added to a solution of 3-(methylaminomethyl)-1H-indole (0.60 g, 3.70 mmole) and Et3N (1.03 mL, 7.40 mmole) in CH2Cl2 (30 mL) at 0° C. The reaction was held at 0° C. for ten minutes, then was stirred overnight at RT. The solution was concentrated in vacuo and the residue was diluted with water. The solution was extracted with ethyl acetate, and the combined organic extracts were washed with brine and dried over Na2SO4. The title compound (0.64 g, 80%) was obtained as a light yellow solid: MS (ES) m/e 215 (M+H)+.

Workup

  1. waitThe reaction was held at 0° C. for ten minutes
  2. concentrationThe solution was concentrated in vacuo
  3. additionthe residue was diluted with water
  4. extractionThe solution was extracted with ethyl acetate
  5. washthe combined organic extracts were washed with brine
  6. dry with materialdried over Na2SO4

Sources & evidence

ORD record
ord-6368c9b4c80946d4964cb4e05ee84d71
Source dataset
uspto-grants-2012_04
Patent number
US08153652B2

Reaction notes

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