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The preparation of carbon‐ 14 labeled tobacco constituents 1 . II. The synthesis of D1‐nicotine (2′‐ 14 C)
Author(s) -
Comes R. A.,
Core M. T.,
Edmonds M. D.,
Edwards W. B.,
Jenkins R. W.
Publication year - 1973
Publication title -
journal of labelled compounds
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0022-2135
DOI - 10.1002/jlcr.2590090206
Subject(s) - nicotine , chemistry , ketone , formamide , carbon 14 , lithium (medication) , nicotinamide , medicinal chemistry , nuclear chemistry , radiochemistry , organic chemistry , medicine , physics , quantum mechanics , neuroscience , biology , enzyme , endocrinology
A 3‐step synthesis, of dl ‐nicotine (2 1 ‐ 14 C) is described. Commercially available nicotinamide (carbonyl‐ 14 C) is dehydrated to 3‐cyanopyridine (cyano‐ 14 C). Reaction of the 3‐cyanopyridine with cyclopropyl lithium yields 3‐pyridyl cyclopropyl ketone (carbonyl‐ 14 C) which is converted to dl ‐nicotine (2 1 ‐ 14 C) by refluring in N‐methyl formamide. Gas‐liquid radio‐chromatography is used for cheimical and radiochemical purity determinations.