Ethanol → N-[2-(4-Hydroxymethylphenyl)-1-methylethyl]-2-hydroxy-2-phenyl ethanamine

Participants

Reaction Steps

A mixture of 1-(4-hydroxymethylphenyl)propan-2-one (3.0 g) and 2-hydroxy-2-phenylethanamine (2.5 g) in benzene (200 ml) was refluxed for 4 hours under Dean and Stark conditions. The solvent was replaced with ethanol (200 ml), platinum oxide (200 mg) was added and the mixture was hydrogenated at ambient temperature and pressure. The solution was filtered and evaporated to give an oil which was taken up in propan-2-ol and treated with the theoretical amount of fumaric acid. The title compound was obtained as the hemi-fumarate salt m.p. 67°-70° (60:40 mixture of diastereoisomers).

Provenance & Evidence