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14C-labeling of a novel anxiolytic agent tandospirone

✍ Scribed by Kazuhiko Nishioka; Hiroshi Kanamaru

Publisher
John Wiley and Sons
Year
1992
Tongue
French
Weight
388 KB
Volume
31
Category
Article
ISSN
0022-2135

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✦ Synopsis

Abstract

N‐[4‐[4‐(2‐Pyrimidinyl)‐1‐piperazinyl]butyl]bicyclo‐[2.2.1]heptane‐2,3‐di‐exo‐carboxyimide dihydrogen citrate (tandospirone), a novel anxiolytic agent, was labeled with carbon‐14 individually at the imido carbonyl group and the pyrimidinyl ring. The synthesis of carbonyl‐labeled tandospirone was achieved according to the scheme shown in Fig. 3. Diels‐Alder reaction of maleic anhydride (2) with cyclopentadiene (3) afforded the endo anhydride (4), which was transformed into the imide (5) by treating with ammonia water. Thermal isomerization of the endo imide (5) and subsequent chromatographic separation gave the pure exo compound (6). Catalytic hydrogenation of 6 followed by alkylation with 1,4‐dibromobutane (8) yielded the bromide (9a). Condensation of 9a with N‐(2‐pyrimidinyl)piperazine (10a) followed by treatment of the resulting disubstituted piperazine (11a) with citric acid afforded [carbonyl‐^14^C]tandospirone (1a). The overall yield of 1a was 22% from 2.

The similar method was applied to the synthesis of pyrimidinyl‐labeled tandospirone as shown in Fig. 4. Condensation of 2‐chloro[2‐^14^C]pyrimidine (12) with anhydrous piperazine gave the pyrimidinylpiperazine (10b). N‐alkylation of 10b followed by treatment with citric acid afforded [pyrimidinyl‐2‐^14^C]tandospirone (1b). The overall yield of 1b was 68% from 12.

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