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Synthesis of 14 C labelled heptacaine and carbisocaine, new local anaesthetics
Author(s) -
Elbert Tomáš,
Marko Vladimír,
Filip Jiří,
Beneš Luděk
Publication year - 1984
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/jlcr.2580210203
Subject(s) - chemistry , heptane , chloride , ethyl chloride , medicinal chemistry , nuclear chemistry , chromatography , radiochemistry , organic chemistry
The published four step synthesis of N‐{2‐(2‐heptyloxyphenyl‐carbamoyloxy)‐ethyl}‐piperidinium chloride ( 5 ) and N‐{2‐(2‐heptyl‐oxyphenylcarbamoyloxy)‐propyl}‐diethylammonium chloride ( 6 ), which starts from o‐acetamidophenol and 1‐bromoheptane was scaled down and modified for radioisotope work. After chromatography 1064 MBq (28,7 mCi) of [heptyl‐1‐ 14 C]heptacaine 5 and 840 MBq (22, 6 mCi) of [heptyl‐1‐ 14 C]carbisocaine 6 were isolated. Radiochemical yields of 5 and 6 on starting 1‐bromo [1‐ 14 C] heptane were 30% and 25%, respectively.