Synthesis of [18F]GBR 12909, a dopamine reuptake inhibitor

Preparation of no-carrier-added fluorine-18 labeled GBR 12909 (1-[2-(bis(4-fluorophenyl)methoxy)ethyl]-4-(3-phenylpropyl)piperazine), a specific and highly affinity inhibitor of dopamine reuptake, is described. 4-Fluoro-4'-[18F]fluorobenzophenone was prepared by [18F]fluoride ion substitution of the corresponding trimethyl-ammonium trifluoromethanesulfonate salt. The [18F]benzophenone was reduced to the benzhydrol, chlorinated, then used to alkylate 1-(2-hydroxyethyl)-4-(3-phenyl-propyl)piperazine to yield [18F]GBR 12909 in high specific activity (>2000 Ci/mmol) and overall yields of 10-16%. (author)