Benzoyl chloride → N-(4-benzyl-4-dimethylaminocyclohexyl)-N-propylbenzamide hydrochloride

Participants

Reaction Steps

700 mg of the nonpolar diastereomer of 1-benzyl-N,N-dimethyl-N′-propyl-cyclohexane-1,4-diamine were dissolved in 10 ml methylene chloride, and 370 μl triethylamine and approx. 10 mg DMAP (4-dimethylaminopyridine) were added. 311 μl benzoyl chloride were added dropwise, while cooling in an ice/methanol bath, and the reaction mixture was then stirred overnight, while warming to room temperature. For working up, 10 ml five molar KOH solution and 10 ml water were added, the mixture was stirred for ten minutes and extracted three times with 20 ml methylene chloride each time, the combined extracts were dried over magnesium sulfate and filtered and the filtrate was concentrated. From the crude product obtained (834 mg), 909 mg N-(4-benzyl-4-dimethylamino-cyclohexyl)-N-propyl-benzamide hydrochloride were prepared as described for example 1 with water and chlorotrimethylsilane in 2-butanone.

Provenance & Evidence