Isolation and identification of three by-products found in methylamphetamine synthesized by the Emde route

This article describes the isolation and structural elucidation of three compounds produced during the synthesis of methylamphetamine by the so-called "Emde" procedure. The "Emde" procedure involves the preparation of the intermediate chloropseudoephedrine or chloroephedrine from ephedrine or pseudoephedrine, respectively. The intermediates are then reduced to methylamphetamine with hydrogen under pressure in the presence of a catalyst. The by-product compounds were isolated from methylamphetamine by column chromatography and liquid chromatography (LC). Proton nuclear magnetic resonance spectroscopy ((1)H NMR), carbon nuclear magnetic resonance spectroscopy ((13)C NMR), and nanospray quadrupole-time of flight-mass spectrometry (Q-TOF-MS) were used to identify them as two stereoisomers of the compound N, N'-dimethyl-3,4-diphenylhexane-2,5-diamine and N-methyl-1-{4-[2-(methylamino)propyl]phenyl}-1-phenylpropan-2-amine.