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Synthesis of N-(4-pyridyl[14C]carbonylamino)-1,2,[3H]3,6-tetrahydropyridine and the mono-labelled [14C]- and [3H]-analogues

✍ Scribed by J. R. Mercer; L. I. Wiebe; E. E. Knaus

Publisher
John Wiley and Sons
Year
1981
Tongue
French
Weight
297 KB
Volume
18
Category
Article
ISSN
0022-2135

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✦ Synopsis

Abstract

Reaction of isonicotinic [^14^C] acid hydrazide (1) with the Zinke salt (2) afforded N‐(4‐pyridyl [^14^C] carbonylimino)pyridinium ylide (3) in 81% chemical yield. Sodium borohydride reduction of 3 gave N‐(4‐pyridyl [^14^C] carbonylamino) −1,2,3,6‐tetrahydropyridine (4) in 60% chemical yield with a specific activity of 6.17 mCi mM^−1^. Alternatively reduction of N‐(4‐pyridylcarbonylimino) pyridinium ylide (5) using absolute ethanol and [^3^H]‐water as solvent yielded N‐ (4‐pyridylcarbonylamino)‐1,2,[^3^H]3,6‐tetrahydropyridine (9) in 52.6% chemical yield with a specific activity of 1.14 mCi mM^−1^. N‐4‐Pyridyl[^14^C]carbonylamino‐1,2,[^3^H]3,6‐ tetrahydropyridine (10) was similarly prepared by sodium borohydride reduction of 3 using absolute ethanol and [^3^H]‐water as solvent in 46% chemical yield with specific activities of 1.31 and 5.66 mCi mM^−1^ respectively for [^3^H] and [^14^C].

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