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Labeling of neuroleptic butyrophenones part 1 synthesis of haloperidol carbon 14 and trifluperidol carbon 14/



Labeling of neuroleptic butyrophenones part 1 synthesis of haloperidol carbon 14 and trifluperidol carbon 14/



Journal of Labelled Compounds and Radiopharmaceuticals 14(1): 133-140



4-[4-(4-Chlorophenyl)-4-hydroxypiperidino]-4'-fluorobutyrophenone (haloperidol) (I) and 4'-fluoro-4-[4-hydroxy-4-(3-trifluoromethylphenyl)piperidino]butyrophenone (trifluperidol) (II), neuroleptic drugs, were labeled at the carbonyl position with 14C for the use of metabolic studies. Cyclopropionic-1-14C acid (IV) was prepared from cyclopropyl bromide by Grignard reaction with 14C-CO2. Condensation of IV with fluorobenzene, followed by ring-opening with hydrogen chloride, gave 4-chloro-4'-fluorobutyrophenone-1-14C (VI). After ketalization of VI, the ketal was condensed with corresponding piperidine derivatives and subsequently hydrolized with HCL to give haloperidol-1-14C (I) and trifluperidol-1-14C (II), respectively. The overall radiochemical yields of I and II from barium carbonate-14C were 31 and 27%, respectively.

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