Selective N-dealkylation of tertiary amines derived from phenylglycinol or ephedrine family

Article abstract of DOI:10.1016/S0040-4039(99)00594-8

Tertiary mines bearing an hydroxyethyl group derived from phenylglycinol, norephedrine or norpseudoephedrine can be selectively dealkylated using a two-step sequence involving treatment with thionyl chloride in THF, followed by reaction with an excess of potassium cyanide in THF:DMSO. These conditions are compatible with the presence of an insaturation or a benzyl ether in the substrate.