3-Benzhydrylmorpholine

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

3-Benzhydrylmorpholine

Identifiers
IUPAC name 3-(Diphenylmethyl)morpholine
CAS Number	93406-27-0 Y
PubChem CID	57466051
ChemSpider	27289065
UNII	ZMZ9TR3HUR
CompTox Dashboard (EPA)	DTXSID60726714
Chemical and physical data
Formula	C17H19NO
Molar mass	253.345 g·mol−1
3D model (JSmol)	Interactive image
SMILES C1(C(C2=CC=CC=C2)C3NCCOC3)=CC=CC=C1
InChI InChI=1S/C17H19NO/c1-3-7-14(8-4-1)17(15-9-5-2-6-10-15)16-13-19-12-11-18-16/h1-10,16-18H,11-13H2 Key:OVLYYUBKZWEOEQ-UHFFFAOYSA-N
(verify)

Synthesis

Patent:^[2]

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.).