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Synthesis and NMR spectral studies ofN-chloroacetyl-2,6-diarylpiperidin-4-ones

Authors
Journal
Spectrochimica Acta Part A Molecular and Biomolecular Spectroscopy
1386-1425
Publisher
Elsevier
Publication Date
Volume
68
Issue
5
Identifiers
DOI: 10.1016/j.saa.2007.01.013
Keywords
  • 1H Nmr
  • 13C Nmr
  • 2D Techniques
  • Conformation
  • Substituent Effect
  • 2
  • 6-Diarylpiperidin-4-Ones
  • Chloroacetylation
Disciplines
  • Chemistry

Abstract

Abstract A series of 2,6-diarylpiperidin-4-ones having electron withdrawing chloroacetyl group at the heterocyclic nitrogen were synthesized. Unambiguous characterizations of the synthesized compounds were achieved by one-dimensional ( 1H NMR and 13C NMR) and two-dimensional (HOMOCOSY, NOESY and HSQC spectra for compounds 8 and 9 and HOMOCOSY spectrum only for 10) NMR spectroscopic data. The conformational preferences of N-chloroacetyl-2,6-diarylpiperidin-4-ones with and without alkyl substituent at C-3 and C-5 ( 8– 14) have also been discussed using the spectral studies. The spectral data and extracted coupling constant values suggest that the compounds 8, 12 and 14 adopt flattened boat conformation whereas the remaining compounds exist in twist-boat conformations in solution with coplanar orientation of the chloroacetyl moiety present at the heterocyclic nitrogen. The substituent parameters for the chloroacetyl moiety on the heterocyclic ring carbons have also been derived and discussed elaborately on the basis of their steric, electronic and γ-eclipsing interaction. This substituent at the nitrogen causes a substantial change on the chemical shifts of ring carbons and the associated protons.

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