10,11-Dihydro-5h-dibenzo[b,e][1,4]diazepine → (4-Cyclohexyl-phenyl)-(5,11-dihydro-10H-dibenzo[b,e][1,4]diazepin-10-yl)methanone

Participants

Reaction Steps

To a suspension of 4-cyclohexylbenzoic acid (10.0 g) in dichloromethane (75 mL) was added oxalyl chloride (10.0 g) followed by N,N-dimethylformamide (2 drops). The mixture was stirred at room temperature overnight and then all volatiles were removed in vacuo to provide the crude acid chloride (11.0 g). 5,11-Dihydro-10H-dibenzo[b,e][1,4]diazepine (1.96 g) in dichloromethane (50 mL) containing N,N-diisopropylethyl amine (1.3 g) was reacted with the crude 4-cyclohexylbenzoyl chloride prepared as described above (2.22 g). The reaction mixture was kept at room temperature overnight, then washed with water and saturated aqueous sodium bicarbonate. The solution was dried over anhydrous sodium sulfate and filtered through a short column of Magnesol® which was eluted with several additional volumes of dichloromethane. The total effluent was refluxed with the gradual addition of hexane until crystallization was noted. Cooling and filtration afforded the title compound as colorless crystals (1.28 g), m.p. 175-176° C.

Provenance & Evidence