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

Participants

Reaction Steps

A solution of methyl-(1-methyl-1H-indol-2-ylmethyl)amine (2.00 g, 11.5 mmol) in CH2Cl2 (100 mL) was treated with acryloyl chloride (1.03 mL, 12.7 mmol) followed by Et3N (1.8 mL, 13 mmol). After stirring for 2 h, the solution was diluted with CH2Cl2 (100 mL) and washed with saturated aqueous NaHCO3 (200 mL). The aqueous layer was extracted with CH2Cl2 (200 mL). The combined organic layers were dried over Na2SO4, filtered and concentrated to an orange oil. Purification by flash column chromatography (silica gel, CH2Cl2/MeOH, 99.5:0.5 to 99:1) gave the title compound (2.10 g, 80%) as a tan oil: 1H NMR (300 MHz, CDCl3) δ 7.59-7.56 (m, 1H), 7.32-7.19 (m, 2H), 7.13-7.08 (m, 1H), 6.66-6.57 (m, 1H), 6.47-6.38 (m, 2H), 5.78-5.74 (m, 1H), 4.88-4.74 (m, 2H), 3.69 (s, 3H), 3.06-2.97 (m, 3H); MS (ESI) m/e 229 (M+Hr.

Provenance & Evidence