Hydrochloric Acid → 1-p-Tolyl-cyclopropanecarboxylic acid heptylamide

Participants

Reaction Steps

To a solution of 1-p-tolylcyclopropanecarboxylic acid (5.68 grams) in chloroform (10 mL) was added thionyl chloride (17.0 mmol, 1.26 mL). The resulting mixture was brought to reflux and was allowed to stir for 3 h. The mixture was cooled to room temperature and concentrated to give a yellow oil. The oil was dissolved in dichloromethane (5 mL) and added dropwise to a solution of 1-heptylamine (6.82 mmol, 1.01 mL) and N,N-diisopropylethylamine (6.82 mmol, 1.19 mL) dissolved in dichloromethane (10 mL) cooled to 0° C. The mixture was warmed to room temperature and was allowed to stir for 30 minutes. The solution was poured over 1 N HCl, and the aqueous layer was isolated and extracted with dichloromethane (3×). The organic layers were combined, washed with 2N HCl (1×), brine (1×), dried over anhydrous sodium sulfate and concentrated to a yellow oil which solidified under high vacuum. The solid was crystallized from hexanes to give 1-p-tolyl-cyclopropanecarboxylic acid heptylamide as a white solid (1.0 g, 64%).

Provenance & Evidence