Triethylamine → N-(1,3-Dimethyl-1H-indol-2-ylmethyl)-N-methylacrylamide

HRID 2112721Notes

Reaction equation

HRID 2112721 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([CH3:11])=[C:3]1[CH2:12][NH:13][CH3:14].CCN(CC)CC.[C:22](Cl)(=[O:25])[CH:23]=[CH2:24]>C(Cl)Cl>[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([CH3:11])=[C:3]1[CH2:12][N:13]([CH3:14])[C:22](=[O:25])[CH:23]=[CH2:24]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 13140Acryloyl chlorideHCID 22139131(1,3-dimethyl-1H-indol-2-yl)-N-methylmethanamine

Product 1

HCID 22593810N-(1,3-Dimethyl-1H-indol-2-ylmethyl)-N-methylacrylamideYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of 1,3-dimethyl-2-(methylaminomethyl)indole (1.5 g, 8 mmole), from Preparation 40, and Et3N (1.12 mL, 8 mmole) in CH2Cl2 (75 mL) at 0° C. was added acryloyl chloride (0.65 mL, 8 mmole) dropwise over 5 minutes. The reaction was stirred at 0° C. for 1 hr then was poured into ice water. The organic phase was separated, washed with brine, dried (MgSO4), and concentrated to dryness to give the title compound (1.7 g, 90%) as a yellow oil. This was used without further purification: TLC silica gel (50% EtOAc/hexanes) Rf=0.41.

Workup

  1. customThe organic phase was separated
  2. washwashed with brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-98f38a0c33d641ae8ba81f4560ec22ab
Source dataset
uspto-grants-2009_04
Patent number
US07524843B2

Reaction notes

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