3-Benzhydrylmorpholine

3-Benzhydrylmorpholine

3-Benzhydrylmorpholine
Systematic (IUPAC) name
3-(diphenylmethyl)morpholine
Clinical data
Legal status
?
Identifiers
CAS number  YesY
ATC code ?
ChemSpider
Chemical data
Formula C17H19NO 
Mol. mass 253.338 g/mol
 YesY   

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.

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

  1. ^ U.S. Patent 2,993,895