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Synthesis of antiarrhythmic [phenyl‐ 14 C]4′‐[(4‐piperidyl)carbonyl]‐methanesulfonanilides
Author(s) -
Oinuma Hitoshi,
Miyake Kazutoshi,
Yamanaka Motosuke,
Shino Mitsumasa,
Hamano Sachiyuki
Publication year - 1990
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.2580280806
Subject(s) - chemistry , aniline , amine gas treating , hydrochloride , pyridine , medicinal chemistry , alkylation , stereochemistry , organic chemistry , catalysis
Syntheses of [phenyl‐ 14 C]4′‐[[1‐[2‐(6‐Methyl‐2‐pyridyl)ethyl]‐4‐piperidyl]carbonyl]methanesulfon‐anilide dihydrochloride dihydrate ( 1 ) ( 14 C‐E‐4031) and its pyridylpropyl analogue ( 2 ), that are selective class III antiarrhythmic agents, are described. A modified Michael reaction of ( 6 ), a key intermediate amine prepared from [U 14 C]aniline hydrochloride, with 6‐methyl‐2‐vinylpyridine ( 7 ) and alkylation of ( 6 ) with 4‐(3‐chloropropyl) pyridine ( 8 ) respectively produced compounds, ( 1 ) and ( 2 ), in satisfactory yields.