Synthesis of carbon‐14 labeled cilobamine mesylate

Cilobamine mesylate, cis-2-(3,4-dichlorophenyl-UL14C)-3-[(1-methylethyl)-amino]bicyclo[2.2.2]octan-2-01 methanesulfonate 1, a new antidepressant, was synthesized in 15% yield from the Grignard reaction of 1-bromo-3,4-dichloro-benzene-UL14C and 3-[(1-methylethyl)amino]bicyclo[2.2.2]octan-2-one, 5. The bicycloketoamine 5 was prepared in three steps from bicyclo[2.2.2]oct-2-ene.