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Synthesis of 14C-labeled and 2H-labeled dibucaine

✍ Scribed by Naba K. Chaudhuri

Publisher
John Wiley and Sons
Year
1985
Tongue
French
Weight
329 KB
Volume
22
Category
Article
ISSN
0022-2135

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✦ Synopsis

A synthesis of dibucaine labeled with l"C in the heterocyclic ring is described. starting with isatin and acetic anh~dride-2-~"C as shown in Scheme I. Two deutero analogs, dibucaine-d2 and dibucaine-dg, were also synthesized by the reactions shown in Scheme 11. Dibucaine-dg was synthesized by condensation of L-chloro-N-[2-(diethylamino)ethyl]- 4-quinoline carboxamide with sodium salt of n-butyl-dg alcohol. Dibucaine-d2 was synthesized by condensation of 2-chloroquinoline carboxylic acid chloride with N,N-diethyl dideutero-ethylenediamine (prepared from chloroacetyl chloride) followed by reaction with sodium n-butoxide. considerable radiolysis on storage to give 2-butoxy-quinoline-4carboxamide as a major decomposition product.

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