Dimethylamine → 3-(N,N-Dimethylamino)methylpyridine-2-carbonitrile

Participants

Reaction Conditions

Reaction Steps

A solution of 3-bromomethylpyridine-2-carbonitrile (591 mg, 3.0 mmol) in MeCN (10 mL) was treated with dimethylamine (7.9-M in water, 1.9 mL, 15 mmol) and heated at 50° C. for 4 h. The solution was treated with MP-carbonate (2.0 g, 6.0 mmol), stirred for 30 min, filtered through Celite and the residue was washed with EtOAc. The filtrate was concentrated in vacuo, and the crude product was purified by chromatography [SiO2; MeOH:EtOAc:isohexane (0:4:1-1:9:0)] to give the title compound (541 mg, 96%) as an orange oil; NMR δH (400 MHz, CDCl3) 2.31 (6H, s), 3.67 (2H, s), 7.50 (1H, dd, J 8.0, 4.5 Hz), 7.94 (1H, dd, J 8.0, 1.5 Hz) and 8.61 (1H, dd, J 4.5, 1.5 Hz); M/Z 162 (M+H)+.

Provenance & Evidence