3-Benzhydrylmorpholine is a drug that was developed by American Home Products in the 1950s.Adderall alternatives It has stimulant and anorectic effects and is related to both pipradrol and phenmetrazine.
Synthesis
The Ethyl ester of β-Phenylphenylalanine (Diphenylalanine), i.e. ethyl 2-amino-3,3-diphenylpropanoate (CID:101017845) (1) is the starting material. Lithium aluminium hydride reduction of the ester to the primary alcohol gives 2-amino-3,3-diphenylpropan-1-ol, CID:15798949 (2). Acylation of the primary amine with chloroacetyl chloride [79-04-9] (3) gives 2-chloro-N-(3-hydroxy-1,1-diphenylpropan-2-yl)acetamide (4). Base catalyzed ring closure affords the lactam, i.e. 5-benzhydrylmorpholin-3-one (5). Further treatment with lithium aluminium hydride reduces the lactam function to the morpholine ring, thus 3-benzhydrylmorpholine is formed (6).
See also Desoxypipradrol β-Phenylmethamphetamine 2-Benzhydrylpiperazine 3-Benzylmorpholine is also patented (q.v.).
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