Water → 1-(4-Chlorophenyl)-3-azabicyclo[3.1.0]hexane Hydrochloride

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Reaction Steps

To a stirred solution f 30 ml of sodium bis(2-methoxyethoxy)aluminum hydride (70% benzene solution) is added dropwise a solution of 2.2 g of 1-(p-chlorophenyl)-1,2-cyclopropanedicarboximide in 100 ml of benzene over a 30 minute period at room temperature under nitrogen atmosphere. The reaction vessel is warmed slightly to maintain solution. The clear yellow solution is then heated to reflux under nitrogen atmosphere for one hour. The solution is cooled and the excess reagent decomposed with 5N sodium hydroxide. Water is added to the mixture and the benzene phase is separated. The aqueous phase is extracted with ether and the ether extracts are combined with the benzene phase and dried over magnesium sulfate. This organic phase is evaporated under reduced pressure to give a viscous liquid, which crystallizes to a tacky off-white solid consisting of the racemic base 1-(p-chlorophenyl)-3-azabicyclo[3.1.0]hexane. This solid is dissolved in ethanol, acidified with ethanolic hydrogen chloride, and ether is added producing off-white crystals of the hydrochloride. This is recrystallized from ethanol giving off-white crystals, mp 215°-217° C.

Provenance & Evidence