Structure via PubChem · Public domain (PubChem)
3-benzhydrylmorpholine
Sign in to saveAlso known as 3-(diphenylmethyl)morpholine
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.
Chemical data
- Formula
- C17H19NO
- Molecular weight
- 253.34 g/mol
- IUPAC name
- 3-benzhydrylmorpholine
- SMILES
- C1COCC(N1)C(C2=CC=CC=C2)C3=CC=CC=C3
- InChIKey
- OVLYYUBKZWEOEQ-UHFFFAOYSA-N
- XLogP
- 2.9
- Polar surface area
- 21.3 Ų
- H-bond donors
- 1
- H-bond acceptors
- 2
- Formal charge
- 0
via PubChem
Wikidata facts
- Subclass of
- chemical compound
- Mass
- 253.146664228
Show 3 more facts
- chemical formula
- C₁₇H₁₉NO
- canonical SMILES
- C1COCC(N1)C(C2=CC=CC=C2)C3=CC=CC=C3
- Commons category
- 3-Benzhydrylmorpholine
via Wikidata · CC0
~1 min read
Encyclopedic overview
3 sectionsContents
- Synthesis
- See also
- References
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== class=skin-invert-image|500px|thumb|center|Patent: 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).
Excerpted from Wikipedia’s “3-benzhydrylmorpholine” article, available under the CC BY-SA 4.0 licence.