Detailed investigations into the Akabori–Momotani reaction for the synthesis of amphetamine type stimulants: Part 2

David Doughty, Emma Kent, Ben Painter, Paul Pigou, Martin Johnston

    Research output: Contribution to journalArticlepeer-review

    1 Citation (Scopus)

    Abstract

    The Akabori–Momotani reaction can be used to synthesise pseudoephedrine in 50% yield from N-methylalanine and benzaldehyde. This paper investigates electronic effects of substituted benzaldehydes on the reaction to synthesise amphetamine type stimulants and identifies several new Akabori–Momotani by-products, 1-[(4-methoxybenzyl)(methyl)amino]ethanol (11c), 2-(4-methoxyphenyl)-3,4-dimethyl-1,3-oxazolidine (12c), 1,2,3,4-tetramethyl-5,6-di-(4-methoxyphenyl)piperazine (13c) and 1,2,4,5-tetramethyl-3,6-di-(4-methoxyphenyl)piperazine (14c). This paper also investigates pseudoephedrine and methamphetamine isomeric distribution from the Akabori–Momotani reaction with the aid of molecular modelling to understand why more pseudoephedrine than ephedrine is produced.

    Original languageEnglish
    Pages (from-to)207-216
    Number of pages10
    JournalForensic Science International
    Volume287
    DOIs
    Publication statusPublished - Jun 2018

    Keywords

    • Akabori-Momotani reaction
    • Clandestine synthesis
    • Ephedrine
    • Pseudoephedrine

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