I. Nakatsuka, K. Kawahara, A. Yoshitake
Apr 1, 1981
Citations
0
Influential Citations
6
Citations
Journal
Journal of Labelled Compounds and Radiopharmaceuticals
Abstract
2′-Amino-4′ -fluoro-4-(4-hydroxy-4-) (3-trifluoromethylphenyl) - piperidino-2-14Cbutyrophenone [ID-4708- (piperidine-14C]), a neuroleptic agent, was synthesized for use in metabolic studies. The synthesis was achieved by the reaction scheme shown in Fig. 1. 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 (8), 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 ID-4708-(piperidine-14 C) (1) in the overall yield of 9.6% from paraformaldehyde-14C.