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Synthesis of 7-chloro-1,3-dihydro-5-(2-fluorophenyl)-1-methyl-2H-1,4-benzodiazepin-2-one-5-14C (fludiazepam-14C)

✍ Scribed by Iwao Nakatsuka; Kazuo Kawahara; Takeshi Kamada; Fumiaki Shono; Akira Yoshitake

Publisher
John Wiley and Sons
Year
1977
Tongue
French
Weight
298 KB
Volume
13
Category
Article
ISSN
0022-2135

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✦ Synopsis

Abstract

7‐Chloro‐1,3‐dihydro‐5‐(2‐fluorophenyl)‐1‐methyl‐2H‐1,4‐benzodiazepin‐2‐one (Fludiazepam) (I), an anti‐anxiety agent, was labelled with carbon‐14 at C‐5 position for metabolic studies. The reaction sequence for the synthesis is shown in Fig. 2. o‐Fluorobenzoic‐^14^C acid (IV) was prepared in 65% yield by carbonation of o‐fluorophenyllithium with carbon‐^14^C dioxide. The acid (IV) was condensed with N‐(4‐chlorophenyl)‐N‐ methylethylenediamine, followed by Bischler‐Napieralski cyclization of the resulting amide with phosphorus pentoxide and phosphorus oxychloride to afford 7‐chloro‐2,3‐dihydro‐5‐(2‐fluorophenyl)‐1‐methyl‐1H‐1,4‐benzodiazepine‐5‐^14^C (VII) in good yield. Oxidation of VII by N‐bromosuccinimide in aqueous solution of sodium bicarbonate gave Fludiazepam‐^14^C (I). The overall yield of I was 24% from barium carbonate‐^14^C.

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