Preparation of remacemide hydrochloride labelled with carbon-14, carbon-13, deuterium and tritium

Abstract

The anti-epileptic agent remacemide hydrochloride has been prepared labelled with 14C, from [carbonyl-14C]acetophenone, and with 13C from [13C6]benzene, [1,2-13C]acetyl chloride and [1-13C]glycine. [2-3H]Glycine was utilised to prepare remacemide labelled with tritium at low specific activity. In addition other 2H- and high specific activity 3H-isotopomers of the drug, and of an active metabolite of the drug, were prepared by hydrogen isotope exchange methodology. The R-12C/S-14C and S-12C/R-14C pseudoracemic drugs were also prepared by a synthesis involving resolution of a 14C-labelled amine intermediate via fractional crystallisation of the dibenzoyltartrate salts. Copyright © 2000 John Wiley & Sons, Ltd.