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Synthesis of 4-amino-5-chloro-N[2-(diethylamino)ethyl]-2- [(butan-2-on-3-yl)oxy]-[carbonyl-14C]benzamide hydrochloride (14C-batanopride)

✍ Scribed by R. T. Standridge; J. E. Swigor

Publisher
John Wiley and Sons
Year
1991
Tongue
French
Weight
263 KB
Volume
29
Category
Article
ISSN
0022-2135

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✦ Synopsis

Abstract

The title compound (1) was synthesized by a 7‐step sequence. 4‐Amino‐2‐hydroxy‐[carbonyl‐^14^C]benzoic acid (1) was selectively methylated to provide the ether ester 2, which was smoothly chlorinated in acetic acid to give 3. The ester was hydrolyzed with aqueous potassium hydroxide to the amino acid 4. This reachted readily, as a mixed anhydride, with diethylaminoethylamine, yielding [^14^C]‐metoclopramide (5). Sodium ethanethiolate in dimethylformamide cleaved the methoxy group cleanly to the phenol (6); this material was not isolated but was condensed in situ with 3‐chloro‐2‐butanone, yielding 7. Formation of the salt with concentrated hydrochloride acid in acetone provided the title compound (8), having a radiochemical purity of 95.6% and a specific activity of 29.8 μCi/mg.

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