Chiral NMR discrimination of the diastereoisomeric salts of the H3-antagonist 2-[3-(1H-imidazol-4-ylmethyl)piperidin-1-yl]-1H-benzimidazole

Magn Reson Chem. 2009 Jun;47(6):515-8. doi: 10.1002/mrc.2418.

Abstract

Diastereomeric salts with optically pure (S)-alpha-methoxy-alpha-(trifluoromethyl)phenylacetic acid (MTPA) were used to discriminate the enantiomers of the chiral H(3)-antagonist 2-[3-(1H-imidazol-4-ylmethyl)piperidin-1-yl]-1H-benzimidazole. Chemical-shift differences (Delta delta) in NMR spectra strongly depend on solvent and stoichiometric ratio. The better observable differentiation occurred for the proton at the 2-position of the imidazole ring.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Benzimidazoles / chemistry*
  • Histamine H3 Antagonists / chemistry*
  • Magnetic Resonance Spectroscopy / methods*
  • Magnetic Resonance Spectroscopy / standards
  • Piperidines / chemistry*
  • Reference Standards
  • Stereoisomerism

Substances

  • 2-(3-(1H-imidazol-4-ylmethyl)piperidin-1-yl)-1H-benzimidazole
  • Benzimidazoles
  • Histamine H3 Antagonists
  • Piperidines