3-Benzhydrylmorpholine


3-Benzhydrylmorpholine is a drug that was developed by American Home Products in the 1950s. It has stimulant and anorectic effects and is related to both pipradrol and phenmetrazine.

Synthesis

The Ethyl ester of β-Phenylphenylalanine, i.e. ethyl 2-amino-3,3-diphenylpropanoate is the starting material. Lithium aluminium hydride reduction of the ester to the primary alcohol gives 2-amino-3,3-diphenylpropan-1-ol, . Acylation of the primary amine with chloroacetyl chloride gives 2-chloro-N-acetamide. Base catalyzed ring closure affords the lactam, i.e. 5-benzhydrylmorpholin-3-one. Further treatment with lithium aluminium hydride reduces the lactam function to the morpholine ring, thus 3-benzhydrylmorpholine is formed.