N,1-dimethylindole-2-carboxamide → methyl((1-methyl-1H-indol-2-yl)methyl)amine

Participants

Reaction Conditions

Reaction Steps

To a solution of N,1-dimethylindole-2-carboxamide (23.3 g, 124.2 mmole) in dry THF (400 mL) was added LiAlH4 (1.0 M in THF, 250 mL, 250 mmole). The reaction solution was heated to 70° C. under argon for 36 hr with stirring. The resulting white cloudy solution was allowed to cool to RT and then was submitted to a basic work-up according to the procedure of Micovic and Mihailovic (Micovic, V. M.; M. L. J. J. Org. Chem. 1956, 18, 1190). Purification by chromatography on silica gel (5% NH4OH in 9:1 CHCl3/MeOH) afforded the titled compound (15.8 g, 73%) as a colorless oil: MS (ES) m/e 175 (M+H)+.

Provenance & Evidence