Water → N-(2-methyl-1H-indol-3-ylmethyl)-N-methylacrylamide

HRID 18309Notes

Reaction equation

HRID 18309 reaction equation
[CH3:1][C:2]1[NH:3][C:4]2[C:9]([C:10]=1[CH2:11][NH:12][CH3:13])=[CH:8][CH:7]=[CH:6][CH:5]=2.C(N(CC)CC)C.[C:21](Cl)(=[O:24])[CH:22]=[CH2:23].O>C(Cl)Cl>[CH3:13][N:12]([CH2:11][C:10]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[NH:3][C:2]=1[CH3:1])[C:21](=[O:24])[CH:22]=[CH2:23]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 13140Acryloyl chlorideHCID 10954023N-Methyl-N-[(2-methyl-1H-indol-3-yl)methyl]amine

Product 1

HCID 22139057N-(2-methyl-1H-indol-3-ylmethyl)-N-methylacrylamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-methyl-3-(methylaminomethyl)indole (1.5 g, 8.6 mmole) and triethylamine (1.7 g, 17.3 mmole) in CH2Cl2 at 5° C. under a nitrogen atmosphere was added acryloyl chloride (0.86 g, 9.48 mmole). After 1 hr the reaction solution was poured into H2O (100 mL) and the layers were separated. The organic fraction was washed with H2O (100 mL) followed by brine and then dried over Na2SO4. Concentration under vacuum gave the title compound as an orange oil which solidified under high vacuum: MS (ES) m/e 457 (2M+H)+. This material was used without further purification.

Workup

  1. customthe layers were separated
  2. washThe organic fraction was washed with H2O (100 mL)
  3. dry with materialdried over Na2SO4
  4. concentrationConcentration under vacuum

Sources & evidence

ORD record
ord-bae101756cb74c45be3bb65c88d4d3f8
Source dataset
uspto-grants-2010_06
Patent number
US07741339B2

Reaction notes

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