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Syntheses of N-[1-2H]- and N-[1-3H]-cyclopropylbenzylamine and [phenyl-14C]-N-cyclopropylbenzylamine

✍ Scribed by Richard B. Silverman; Stephen J. Hoffman

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

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✦ Synopsis

Abstract

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.

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