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Labeling of neuroleptic butyrophenones 3. synthesis of carbon 14 labeled 2' amino 4' fluoro 4 4 hydroxy 4 3 trifluoromethylphenylpiperidino butyrophenone



Labeling of neuroleptic butyrophenones 3. synthesis of carbon 14 labeled 2' amino 4' fluoro 4 4 hydroxy 4 3 trifluoromethylphenylpiperidino butyrophenone



Journal of Labelled Compounds and Radiopharmaceuticals 18(4): 495-506



2'-Amino-4'-fluoro-4-[4-hydroxy-4-(3-trifluoromethylphenyl)piperidino-2-14C]butyrophenone [ID-4708-(piperidine-14C)] (1), a neuroleptic agent, was synthesized for use in metabolic studies [in animals]. The synthesis was achieved by the reaction scheme which is described. 1-Benzyl-4-piperidone-2-14C was prepared by Mannich reaction of paraformaldehyde-14C with ethyl acryloylacetate and benzylamine, followed by treatment with hydrochloric acid, in 65% yield. Grignard reaction of the product with 3-trifluoromethylphenyl-magnesium bromide followed by hydrogenolysis gave 4-hydroxy-4-(3-trifluoromethylphenyl)piperidine-2-14C, which was condensed with 3-(6-fluoro-2-methyl-3-indolyl)propionic acid to give the 3-indolylpropionylpiperidine-14C (10). Conversion of 10 by reduction, oxidation and then hydrolysis led to (1) in the overall yield of 9.6% from paraformaldehyde-14C.

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