Diethyl Ether → HCID 23459455, compound

Participants

Reaction Steps

0.68 g. of aluminum trichloride and 0.24 g. of lithium aluminum hydride are placed in 8 ml. of absolute ether. 1 g. of 1-phenyl-2,5-cyclohexadien-1-acetonitrile in 5 ml. of absolute ether is added dropwise while stirring. After stirring at room temperature for 2 hours, the mixture is worked-up as follows: The mixture is treated with 1 ml. of water and 25 ml. of 3 N aqueous sodium hyroxide, filtered under suction and the filter rinsed with ether. After separating the phases, the organic phase is dried over sodium sulfate, filtered and concentrated to dryness. The crude product obtained is chromatographed on 50 g. of Alox (neutral), educt being first of all eluted with ether and then end product being eluted with methylene chloride/methanol (10:1). There is obtained 1-phenyl-2,5-cyclohexadien-1-ethylamine as an oily product. 3 g. of this product are converted in the usual manner into the hydrochloride which, after recrystallization from methylene chloride/ether, has a melting point of 170°-172° C.

Provenance & Evidence