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

HRID 1826025Notes

Reaction equation

HRID 1826025 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-9881b35aa2b74a1e948f9fb847123332
Source dataset
uspto-grants-2006_05
Patent number
US07049310B2

Reaction notes

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