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3-Benzhydrylmorpholine

Chemical compound

3-Benzhydrylmorpholine

Chemical compound

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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

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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).

References

References

  1. [https://campuspress.yale.edu/wave/best-adderall-alternatives-the-top-rated-otc-natural-focus-pills/ Adderall alternatives]
  2. "3-Benzhydrylmorpholine and salts thereof, and method of preparing said compounds".
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stimulants morpholines benzhydryl-compounds
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