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3-Benzhydrylmorpholine

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3-Benzhydrylmorpholine
File:3-BZHM structure.png
Systematic (IUPAC) name
3-(diphenylmethyl)morpholine
Clinical data
Identifiers
93406-27-0 7pxY
ChemSpider 27289065
Chemical data
Formula C17H19NO
253.338 g/mol
 14pxY (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

It is made from Diphenylalanine starting material.

File:3-Benzhydrylmorpholine synthesis.svg
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

References


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