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

•Substituted benzaldehydes convert into pseudoephedrines.•Electronic influence of the substituent on reaction outcomes was minor.•Molecular modelling provides insight into substituents lack of influence.•Sub-optimal reaction conditions with p-methoxy benzaldehyde produce new by-products.•Stereochemical purity of products rationalised by molecular modelling. 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.