Synthesis of 13C, 14C and 2H13C labeled adrenoceptor antagonists: 6-chloro-2,3,4,5-tetrahydro-3-methyl-1H-3-benzazepine hydrochloride and its N-desmethyl analog

The compound 6-chloro-2,3,4,5-tetrahydro-3-methyl-1H-3-benzazepine (SK&F 86466) was prepared in phenyl-U-14C and phenyl-13C6 labeled forms in a six step sequence beginning with the appropriately labeled benzenes. In addition, the N-desmethyl analog of the carbon-14 labeled isotopomer and the N-methyl-2H3 derivative of the carbon-13 isotopomer were prepared via the N-(2,2,2-trichloroethyl) carbamates by hydrolysis and lithium aluminum deuteride reduction, respectively.