Phenethyl bromide → 9-(2-Phenylethyl)-2,3,9,10a-tetrahydrobenzo[b]-cyclopenta[e][1,4]diazepin-10(1H)-one

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Reaction Steps

A solution of 2,3,9,10a-tetrahydrobenzo[b]-cyclopenta[e][1,4]diazepin-10(1H)-one (5.01 g, 25 mmol) in N,N-dimethylformamide (30 mL) was cooled to 0° C. To the solution was added sodium hydride (60% liquid paraffin dispersion, 1.0 g, 25 mmol). The mixture was stirred for 5 minutes at the same temperature and for 10 minutes at room temperature. To this solution was added a solution of 2-(bromoethyl)benzene (5.09 g, 27.5 mmol) in N,N-dimethylformamide (1 mL), and the mixture was stirred for 2.5 hours at room temperature. The reaction mixture was poured into a saturated aqueous solution of ammonium chloride (40 mL), which was diluted with water, followed by extraction twice with ethyl acetate. Organic layers were combined and washed with water and a saturated aqueous solution of sodium chloride, which was dried by allowing to pass through magnesium sulfate and silica-gel, followed by concentration under reduced pressure. Unreacted diazepinone was allowed to crystallize, and most portion of which was removed. The remainder was purified by silica-gel column chromatography (hexane-ethyl acetate 20:1, later 5:1), followed by recrystallization from ethyl acetate-hexane to afford the titled compound (2.37 g, 31%), m.p.101°-102° C.

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