Water → N-methyl-N-(1,2,7-trimethyl-1H-indol-3-ylmethyl)acrylamide

HRID 1826045Notes

Reaction equation

HRID 1826045 reaction equation
[CH3:1][NH:2][CH2:3][C:4]1[C:12]2[C:7](=[C:8]([CH3:13])[CH:9]=[CH:10][CH:11]=2)[N:6]([CH3:14])[C:5]=1[CH3:15].CCN([CH2:21][CH3:22])CC.[OH2:23].[CH2:24](Cl)Cl>>[CH3:1][N:2]([CH2:3][C:4]1[C:12]2[C:7](=[C:8]([CH3:13])[CH:9]=[CH:10][CH:11]=2)[N:6]([CH3:14])[C:5]=1[CH3:15])[C:24](=[O:23])[CH:21]=[CH2:22]

Participants

5

Reactant 4

HCID 962WaterHCID 6344DichloromethaneHCID 8471TriethylamineHCID 110090053-(methylaminomethyl)-1,2,7-trimethyl-1H-indole

Product 1

HCID 66905360N-methyl-N-(1,2,7-trimethyl-1H-indol-3-ylmethyl)acrylamideYield 97%

Procedure

To a cold solution (ice bath) of 3-(methylaminomethyl)-1,2,7-trimethyl-1H-indole (570 mg, 2.8 mmole) in dry CH2Cl2 (24 mL) was added dry Et3N (0.25 mL, 2.9 mmole). The reaction was stirred in the cold under argon for 2 h then was poured into H2O (40 mL). The layers were separated, and the organic layer was washed with brine, dried (MgSO4), filtered, and concentrated. The title compound (0.7 g, 97%) was obtained as a light orange solid: MS (ES) m/e 257.2 (M+H)+.

Workup

  1. customThe layers were separated
  2. washthe organic layer was washed with brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-831ce2b047414368afcce8157365935f
Source dataset
uspto-grants-2006_05
Patent number
US07049310B2

Reaction notes

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