Convenient, benign and scalable synthesis of 2- and 4-substituted benzylpiperidines

Béla Ágai, Ágnes Proszenyák, Gábor Tárkányi, László Vida, Ferenc Faigl

Research output: Contribution to journalArticle

21 Citations (Scopus)

Abstract

A short, scalable and environmentally benign synthesis of 2- and 4-substituted benzylpiperidines has been developed. The method is based on the temperature-programmed consecutive deoxygenation and heteroaromatic ring saturation of aryl(pyridin-2-yl)- and aryl(pyridin-4-yl)methanols and aryl(pyridin-4-yl)methanones in the presence of Pd/C catalyst. The crucial roles of the temperature, the acidity and the substrate structure in the change of selectivity have been demonstrated by isolation of several substituted aryl(piperidine)methanols. The carbinols and ketones were prepared from commercially available pyridinecarbaldehydes or 4-cyanopyridine and substituted bromobenzenes via organometallic intermediates.

Original languageEnglish
Pages (from-to)3623-3632
Number of pages10
JournalEuropean Journal of Organic Chemistry
Issue number17
DOIs
Publication statusPublished - Aug 27 2004

    Fingerprint

Keywords

  • Benzylpiperidines
  • Grignard reaction
  • Heterogeneous catalysis
  • Hydrogenation
  • Nitrogen heterocycles

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this