Hydrochloric Acid → HCID 10109604, compound

Participants

Reaction Steps

4-Cyclohex-1-en-1-yl-benzoic acid of Step C (0.099 g, 0.489 mmol) and oxalyl chloride (0.065 g, 0.513 mmol) were dissolved in anhydrous methylene chloride (5 mL) and N,N-dimethylformamide (0.00114 mL, 0.0147 mmol) added. The resulting mixture was refluxed for 1 hour, then cooled to room temperature and solvent evaporated. The crude acid chloride thus prepared was combined with 10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine (0.090 g, 0.489 mmol) and N,N-diisopropyl ethylamine (0.103 mL, 0.589 mmol) in anhydrous dichloromethane (5 mL). After stirring at room temperature for 1.5 hours, 1 N hydrochloric acid (50 mL) was added and the resulting mixture extracted with diethyl ether (50 mL). The organic phase was washed with 1 N hydrochloric acid, 1 N sodium hydroxide and brine. The organic phase was dried over anhydrous magnesium sulfate, filtered and concentrated, and the residue purified by flash column chromatography on silica gel, eluting with 20% ethyl acetate in hexane. A slightly orange solid was isolated which was recrystallized from petroleum ether to afford the title compound (0.131 g) as white crystals, m.p. 156° C.

Provenance & Evidence