Triethylamine → N-Methyl-N-[(1-methyl-2-indolyl)methyl]acrylamide

HRID 1761116Notes

Reaction equation

HRID 1761116 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]1[CH2:11][NH:12][CH3:13].C(N(CC)CC)C.[C:21](Cl)(=[O:24])[CH:22]=[CH2:23]>C(Cl)Cl>[CH3:13][N:12]([CH2:11][C:3]1[N:2]([CH3:1])[C:10]2[C:5]([CH:4]=1)=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:21](=[O:24])[CH:22]=[CH2:23]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 13140Acryloyl chlorideHCID 11401058methyl((1-methyl-1H-indol-2-yl)methyl)amine

Product 1

HCID 20752825N-Methyl-N-[(1-methyl-2-indolyl)methyl]acrylamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-methyl-2-(methylaminomethyl)indole (0.96 g, 5.5 mmole), from Preparation 1, and triethylamine (1.54 mL, 11.0 mmole) in CH2Cl2 (50 mL) at 5° C. was added acryloyl chloride (0.48 mL, 6.0 mmole). After 45 min, the reaction solution was poured onto H2O and the layers were separated. The organic phase was dried over Na2SO4 and concentrated to afford the title compound as a yellow oil. This was used directly without further purification.

Workup

  1. additionthe reaction solution was poured onto H2O
  2. customthe layers were separated
  3. dry with materialThe organic phase was dried over Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-0528b58bfae24c0a90f62a6ac3ddf137
Source dataset
uspto-grants-2005_01
Patent number
US06846819B1

Reaction notes

Loading…