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Preparation of 1-methyl-4-[4-(7-chloro-4-quinolyl-[3-14C]-amino)benzoyl]piperazine

✍ Scribed by Theodore S. T. Wang; Rashid A. Fawwaz; Ronald L. Van Heertum

Publisher
John Wiley and Sons
Year
1995
Tongue
French
Weight
292 KB
Volume
36
Category
Article
ISSN
0022-2135

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✦ Synopsis

1 -M e t h y l -4 -[ 4 -( 7 -c h l o r 0 -4 -q ~n i n o l y l -[ 3 -~~C 1amino)-benzoyllpiperazine (V) was prepared for pharmacokinetic and pharmacodynamic evaluation. The synthesis of V was accomplished first by a modified Claisen ester condensation reaction of diethyl-[2-14C]-malonate, triethyl orthoformate, and acetic anhydride in the presence of ZnC12 to form ethyl etho~yrnethylene-[2-'~C]-malonate (I), which was further condensed with m-chloroaniline to yield

7-chloro-4-hydroxy-3-[14C]-quinoline-ethylcarboxylate (11).

Saponification of I 1 yielded the corresponding carboxylic acid (Ill). Decarboxylation of the acid group upon heating and a substitution of the 4-OH group of compound Ill into chlorine atom with POCI, produced 4,7-dichlor0-[3-'~C]-quinoline (IV), which then was reacted with l-methyl-4-(pamino-benzoy1)piperazine to form the title compound V. There were a total of five steps of reaction, with a overall yield of 34.3%. The specific activity was 1.74 mCi/mmol.

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