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Syntheses of N‐[1‐ 2 H]‐ and N‐[1‐ 3 H]‐cyclopropylbenzylamine and [phenyl‐ 14 C]‐N‐cyclopropylbenzylamine
Author(s) -
Silverman Richard B.,
Hoffman Stephen J.
Publication year - 1981
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.2580180604
Subject(s) - chemistry , sodium cyanoborohydride , sodium methoxide , benzaldehyde , hydrolysis , medicinal chemistry , methanol , sodium , base (topology) , organic chemistry , catalysis , mathematical analysis , mathematics
N‐[1‐ 2 H]‐ ( 5a ) and N‐[1‐ 3 H]‐Cyclopropylbenzylamine ( 5b ) were synthesized from cyclopropanecarbonitrile. The α‐proton of cyclopropanecarbonitrile was exchanged in [O‐ 2 H]‐ and [O‐ 3 H]‐methanol using sodium methoxide as the base. [α‐ 2 H]‐ and [α‐ 3 H]‐Cyclopropanecarbonitrile were hydrolyzed in 4N HCl to the α‐labeled cyclopropanecarboxylic acids which were converted to [1‐ 2 H]‐ and [1‐ 3 H]‐cyclopropylamine. HCl by Curtius rearrangements. The labeled cyclopropylamines were benzylated by reaction with benzaldehyde followed by sodium cyanoborohydride reduction. [phenyl‐ 14 C]‐Cyclopropylbenzylamine ( 2b ) was prepared by the reaction of cyclopropylamine with [phenyl‐ 14 C] benzaldehyde followed by sodium cyanoborohydride reduction.