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

HRID 1921050Notes

Reaction equation

HRID 1921050 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 (0.78 g, 4.5 mmole), from Preparation 1, and triethylamine (1.4 mL, 10.0 mmole) in CH2Cl2 (50 mL) at 5° C. was added acryloyl chloride (0.41 mL, 4.95 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-ba37fa5c06564dc3991eb910b1604a72
Source dataset
uspto-grants-2012_05
Patent number
US08173646B2

Reaction notes

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