[CH2:1]1[CH:10]2[C:4](=[N:5][C:6]3[CH:15]=[CH:14][CH:13]=[CH:12][C:7]=3[NH:8][C:9]2=[O:11])[CH2:3][CH2:2]1.[H-].[Na+].Br[CH2:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.[Cl-].[NH4+]>CN(C)C=O.O>[C:21]1([CH2:20][CH2:19][N:8]2[C:9](=[O:11])[CH:10]3[CH2:1][CH2:2][CH2:3][C:4]3=[N:5][C:6]3[CH:15]=[CH:14][CH:13]=[CH:12][C:7]2=3)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1
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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