Reductive Amination of Ethynylpyridines with Sodium Cyanoborohydride

Takao Sakamoto, Hideo Nagata, Yoshinori Kondo, Kaori Sato, Hiroshi Yamanaka

Research output: Contribution to journalArticlepeer-review

11 Citations (Scopus)


In order to investigate the structure-activity relationship of betahistine derivatives, a general synthesis of methylated 2-(2-methylaminoethyl)pyridines was developed based on the addition of methylamine hydrochloride to methylated 2-ethynylpyridines under reductive conditions. In addition, the scope and limitations of the reductive addition were briefly examined. For example, the reaction proceeded smoothly with p-nitrophenylacetylene, whereas phenylacetylene itself did not react with methylamine.

Original languageEnglish
Pages (from-to)4866-4872
Number of pages7
JournalChemical and Pharmaceutical Bulletin
Issue number12
Publication statusPublished - 1984


  • 2-(2-pyridyl)ethylamine
  • betahistine
  • ethyl pyridineacetate
  • ethynylpyridine
  • palladium-catalyzed reaction
  • reductive amination
  • sodium cyanoborohydride

ASJC Scopus subject areas

  • Chemistry(all)
  • Drug Discovery


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