Benzene → 1-methyl-4-(9-cyano-11H-pyrrolo[2,1-b][3]benzazepin-11-ylidene)piperidine

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Reaction Steps

1-Methyl-4-(9-bromo-11H-pyrrolo[2,1-b][3]benzazepin-11-ylidene)piperidine (6.3 g, 0.019 mole) and cuprous cyanide (3.2 g, 0.035 mole) in 25 ml of dry dimethylformamide are refluxed under nitrogen for five hours. The mixture is cooled to an internal temperature of 50° and treated with 60 ml each of benzene and aqueous saturated sodium cyanide solution. After stirring one hour the contents are transferred to a separatory funnel with the aid of additional benzene and water. The aqueous phase is extracted two times with benzene, once with ether and the combined benzene-ether extracts are washed successively with dilute sodium cyanide, water, dilute ammonium hydroxide, and water. Upon drying over sodium sulfate the solvents are evaporated in vacuo to give 1-methyl-4-(9-cyano-11H-pyrrolo[2,1-b][3]benzazepin-11-ylidene)piperidine as an oil (5.0 g, 87%). Trituration with acetonitrile gives a solid (3.6 g, m.p. 156°-159°). An analytical sample is obtained after one recystallization from acetonitrile, m.p. 158°-161°.

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