Tetrahydrofuran → HCID 178511499, compound

Participants

Reaction Steps

Into a solution of 8.58 g. of 4-phenylcyclohexanone oxime acetate (prepared in Example 79) in 90 ml. of tetrahydrofuran and 27 ml. of t-butanol, 350 ml. of ammonia is distilled from over sodium. To this there is added 1.9 g. of lithium in three portions at a rate that the blue color just persists. When the final blue color fades, 10 g. of solid ammonium chloride is added and the solvent is then evaporated with a stream of nitrogen. The residue is dissolved in ether and aqueous N-sodium hydroxide solution. The organic layer is separated, washed with water and brine and then taken to dryness to give a residue of trans 4-phenylcyclohexylamine. The residue is dissolved in a small amount of ether and treated with an excess of 4.9N hydrogen chloride in ether. The precipitate that forms is collected on a filter to yield 7.9 g. of trans 4-phenylcyclohexylamine hydrochloride. A sample of identical material previously prepared melts above 300° C.

Provenance & Evidence