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Labelling of neuroleptic butyrophenones. III. Synthesis of 2′-amino-4′-fluoro-4-[4-hydroxy-4-(3-trifluoromethylphenyl)piperidino-2-14C] - butyrophenone

✍ Scribed by Iwao Nakatsuka; Kazuo Kawahara; Akira Yoshitake

Publisher
John Wiley and Sons
Year
1981
Tongue
French
Weight
474 KB
Volume
18
Category
Article
ISSN
0022-2135

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✦ Synopsis

Abstract

2′‐Amino‐4′ ‐fluoro‐4‐(4‐hydroxy‐4‐) (3‐trifluoromethylphenyl) ‐ piperidino‐2‐^14^Cbutyrophenone [ID‐4708‐ (piperidine‐^14^C]), 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‐^14^C was prepared by Mannich reaction of paraformaldehyde‐^14^C 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‐^14^C (8), which was condensed with 3‐(6‐fluoro‐2‐methyl‐3‐indolyl) propionic acid to give the 3‐indolylpropionylpiperidine‐^14^C (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‐^14^C.

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