Article · Wikipedia archive · Last revised Jul 18, 2026

3-Benzhydrylmorpholine

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.

Last revised
Jul 18, 2026
Read time
≈ 1 min
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165 w
Citations
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Source
Wikipedia ↗
3-Benzhydrylmorpholine
Identifiers
  • 3-(Diphenylmethyl)morpholine
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC17H19NO
Molar mass253.345 g·mol−1
3D model (JSmol)
  • C1(C(C2=CC=CC=C2)C3NCCOC3)=CC=CC=C1
  • 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)

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.

Synthesis

Patent:2 source ↗

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

See also

References

References

  1. Adderall alternatives
  2. US 2993895, Winthrop SO, "3-Benzhydrylmorpholine and salts thereof, and method of preparing said compounds", issued 25 July 1961, assigned to American Home Prod.