3-Benzhydrylmorpholine
{{Short description|Chemical compound}}
{{Drugbox
| verifiedrevid = 451606038
| IUPAC_name = 3-(Diphenylmethyl)morpholine
| image = 3-Benzhydrylmorpholine.svg
| image_class = skin-invert-image
| tradename =
| pregnancy_AU =
| pregnancy_US =
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| legal_AU =
| legal_CA =
| legal_UK =
| legal_US =
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| bioavailability =
| protein_bound =
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| CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = 93406-27-0
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = ZMZ9TR3HUR
| ATC_prefix =
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| PubChem = 57466051
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank =
| ChemSpiderID = 27289065
| StdInChI = 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
| StdInChIKey = OVLYYUBKZWEOEQ-UHFFFAOYSA-N
| C=17 | H=19 | N=1 | O=1
| smiles = C1(C(C2=CC=CC=C2)C3NCCOC3)=CC=CC=C1
}}
3-Benzhydrylmorpholine is a drug that was developed by American Home Products in the 1950s.[https://campuspress.yale.edu/wave/best-adderall-alternatives-the-top-rated-otc-natural-focus-pills/ Adderall alternatives] It has stimulant and anorectic effects and is related to both pipradrol and phenmetrazine.
Synthesis
File:3-Benzhydrylmorpholine synthesis.svg
The Ethyl ester of β-Phenylphenylalanine (Diphenylalanine), i.e. ethyl 2-amino-3,3-diphenylpropanoate ([https://pubchem.ncbi.nlm.nih.gov/compound/101017845 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, [https://pubchem.ncbi.nlm.nih.gov/compound/15798949 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.).
References
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{{stimulants}}
{{DEFAULTSORT:Benzhydrylmorpholine, 3-}}