Tert-Butylamine → N-tert-butyl-3-(chloromethyl)benzamide

Participants

Reaction Conditions

Reaction Steps

3-(Chloromethyl)benzoyl chloride (20 g, 105.80 mmol) was added to cooled (−30° C.), stirred dichloromethane (60 mL). After 10 minutes stirring, a solution of tert-butylamine (11.1 ml, 105.80 mmol) and N-ethyl-N-Isopropylpropan-2-amine (36.9 mL, 211.60 mmol) in dichloromethane (30 mL) was added dropwise. After complete addition, the reaction was allowed to warm to −15° C. and stir for 90 minutes then was allowed to warm to room temperature. The reaction was concentrated under vacuum and the residue was dissolved in ethyl acetate and washed consecutively with 2M aqueous hydrochloric acid, water (×2) and brine. The organic phase was concentrated under vacuum to give the title compound (19.61 g) as a white solid.

Provenance & Evidence