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

Richard B Silverman*, Stephen J. Hoffman

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

7 Scopus citations

Abstract

N‐[1‐2H]‐ (5a) and N‐[1‐3H]‐Cyclopropylbenzylamine (5b) were synthesized from cyclopropanecarbonitrile. The α‐proton of cyclopropanecarbonitrile was exchanged in [O‐2H]‐ and [O‐3H]‐methanol using sodium methoxide as the base. [α‐2H]‐ and [α‐3H]‐Cyclopropanecarbonitrile were hydrolyzed in 4N HCl to the α‐labeled cyclopropanecarboxylic acids which were converted to [1‐2H]‐ and [1‐3H]‐cyclopropylamine. HCl by Curtius rearrangements. The labeled cyclopropylamines were benzylated by reaction with benzaldehyde followed by sodium cyanoborohydride reduction. [phenyl‐14C]‐Cyclopropylbenzylamine (2b) was prepared by the reaction of cyclopropylamine with [phenyl‐14C] benzaldehyde followed by sodium cyanoborohydride reduction.

Original languageEnglish (US)
Pages (from-to)781-790
Number of pages10
JournalJournal of Labelled Compounds and Radiopharmaceuticals
Volume18
Issue number6
DOIs
StatePublished - Jan 1 1981

Keywords

  • N‐Cyclopropylbenzylamine
  • cyclopropanecarboxylic acid
  • cyclopropylamine

ASJC Scopus subject areas

  • Analytical Chemistry
  • Biochemistry
  • Radiology Nuclear Medicine and imaging
  • Drug Discovery
  • Spectroscopy
  • Organic Chemistry

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