3-Benzhydrylmorpholine

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3-Benzhydrylmorpholine
3-BZHM structure.png
Systematic (IUPAC) name
3-(diphenylmethyl)morpholine
Clinical data
Legal status ?
Identifiers
CAS number 93406-27-0 YesY
ATC code ?
ChemSpider 27289065
Chemical data
Formula C17H19NO 
Mol. mass 253.338 g/mol
 YesY (what is this?)  (verify)

3-Benzhydrylmorpholine was developed by American Home Products Corporation in the 1950s,[1] and is a drug with stimulant and anorectic effects, related to both pipradrol and phenmetrazine.

Synthesis[edit]

It is made from Diphenylalanine starting material.

Preparation of 3-Benzhydrylmorpholine

1. Ethyl ester.
2. LAH reduction to 1° alcohol.
3. React 3,3-diphenyl-2-amino-l-propanol with chloroacetyl chloride to yield 3,3-diphenyl-2-(α-chloro acetylamino)-1-propanol.
4. Cyclize to lactam with KOH to get 5-benzhydryl-3-morpholone.
5. LAH reduction to final product 3-benzhydrylmorpholine.

See also[edit]

References[edit]