Water → N-(2-pyridylmethyl)-5-bromopentanamide

Participants

Reaction Steps

Part A. A solution of 2-(aminomethyl)pyridine (4.07 g, 37.6 mmol) and triethylamine (7.50 mL, 53.8 mmol) in tetrahydrofuran (100 mL) was cooled to 0° C., then treated with a solution of 5-bromovaleryl chloride (5.00 mL, 37.6 mmol) in tetrahydrofuran (20 mL) dropwise. After stirring for 12 hours, the mixture was poured into water (150 mL) and extracted with methylene chloride (2×150 mL). The extracts were combined, dried over anhydrous magnesium sulfate, filtered and evaporated to afford the oily product, N-(2-pyridylmethyl)-5-bromopentanamide (9.44 g, 34.8 mmol, 93%).

Provenance & Evidence