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Synthesis of [methyl‐ 14 C]‐N‐methylputrescine
Author(s) -
Secor H. V.,
Izac R. R.,
Hassam S. B.,
Frisch A. F.
Publication year - 1994
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.2580340503
Subject(s) - methylamine , chemistry , benzaldehyde , radiosynthesis , catalysis , alkylation , regioselectivity , hydrochloride , aqueous solution , yield (engineering) , medicinal chemistry , nuclear chemistry , organic chemistry , in vivo , biology , materials science , metallurgy , microbiology and biotechnology
[Methyl‐ 14 C]‐N‐methylputrescine was prepared from [ 14 C]methylamine hydrochloride in five steps. Reaction of benzaldehyde and [ 14 C]methylamine (10 mCi) followed by catalytic hydrogenation yielded [methyl‐ 14 C]‐N‐methylbenzylamine. The key step in this process is the alkylation of [methyl‐ 14 C]‐N‐methylbenzylamine in aqueous medium with 4‐bromobutyronitrile. The radiochemical purity of the final product after two successive catalytic hydrogenations was in excess of 97%. The radiochemical yields in two successive runs were 26 and 38%, based on starting [ 14 C]methylamine, with specific activities of 22 and 23 mCi/mmol, respectively. This sequence provides a convenient and efficient regioselective radiosynthesis of [methyl‐ 14 C]‐N‐methylputrescine.