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

HRID 1362252Notes

Reaction equation

[C:1](Cl)(=[O:4])[CH:2]=[CH2:3].[CH3:6][NH:7][CH2:8][C:9]1[N:10]([CH3:18])[C:11]2[C:16]([CH:17]=1)=[CH:15][CH:14]=[CH:13][CH:12]=2.C(N(CC)CC)C>C(Cl)Cl>[CH3:6][N:7]([CH2:8][C:9]1[N:10]([CH3:18])[C:11]2[C:16]([CH:17]=1)=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:1](=[O:4])[CH:2]=[CH2:3]

Participants

Conditions

Temperature: -30 °C

Procedure

Acryloyl chloride (5.13 mL, 63.1 mmol) was added dropwise to a stirred CH2Cl2 (100 mL) solution of methyl-(1-methyl-1H-indol-2-ylmethyl)-amine (10.0 g, 57.4 mmol) and triethylamine (12 mL, 86.1 mmol) at −78° C. The reaction mixture was warmed to −30° C. over 30 min and quenched with water. The reaction mixture was diluted with CH2Cl2 (100 mL), washed with dilute NaHCO3, HCl and water, dried and evaporated to afford 9.91 g (76%) title compound. 1H NMR (300 MHz, DMSO-d6) δ 7.44 (m, 2H), 7.12 (t, J=7.2 Hz, 1H), 7.00 (t, J=7.2 Hz, 1H), 6.81 (dd, J=7.4 and 16.7 Hz, 1H), 6.40 and 6.14 (rotamers, 2s, 1H), 6.20 (dd, J=2.5 and 16.7 Hz, 1H), 5.7 (m, 1H), 4.90 and 4.80 (rotamers, 2s, 2H), 3.68 and 3.66 (rotamers, 2s, 3H), 3.00 and 2.96 (rotamers, 2s, 3H). MS (ESI) m/e: 229.1 (M+H)+.

Workup

customquenched with water
additionThe reaction mixture was diluted with CH2Cl2 (100 mL)
washwashed with dilute NaHCO3, HCl and water
customdried
customevaporated

Sources & evidence

ORD record: ord-9a90fbe6985341a28349f6d1a6b0b163
Source dataset: uspto-grants-2011_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07879872B2

Reaction notes

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