Sodium Hydroxide → 1-(p-Chloro-alpha,alpha,alpha-trifluoro-m-tolyl)-3-azabicyclo[3.1.0]hexane hydrochloride

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Reaction Steps

To a solution of 0.28 g. of 1-(p-chloro-α,α,α-trifluoro-m-tolyl)cyclopropanedicarboximide in 10 ml. of benzene is added one ml. of Vitride®. This is refluxed for one hour, cooled to ambient temperature, and the excess hydride reagent is decomposed with one ml. of 10 N sodium hydroxide. The benzene layer is washed with water, dried over magnesium sulfate and evaporated under reduced pressure to give an amber-colored oil. This is dissolved in ether and dry hydrogen chloride is bubbled into the solution. The resultant precipitate is collected by filtration and recrystallized from isopropyl alcohol to give 1-(p-chloro-α,α,α-trifluoro-m-tolyl)-3-azabicyclo[3.1.0]hexane hydrochloride. Purification of the hydrochloride by recrystallization from acetonitrile gives colorless crystals, m.p. 164°-166° C.

Provenance & Evidence