Structure-retention relationship in a series of chiral 1,4-disubstituted piperazine derivatives on carbohydrate chiral stationary phases

Farmaco. 2005 May;60(5):439-43. doi: 10.1016/j.farmac.2005.01.006. Epub 2005 Apr 14.

Abstract

New racemic 1,4-disubstituted piperazines chemically named ethyl 2-[(4-pyrimidin-2yl-piperazine-1yl)carbonyl]C3-C5-alkanoates 1-7 were synthesized. The compounds were resolved into enantiomers on cellulose tris(4-methylbenzoate) and amylose tris(3,5-dimethylphenylcarbamate) stationary phases using hexane/propan-2-ol mobile phases. The optimum separation conditions for the compounds were obtained on cellulose tris(4-methylbenzoate) with 5% of 2-propanol in hexane. The relationship between structural and chromatographic parameters is discussed.

MeSH terms

  • Amylose / analogs & derivatives
  • Amylose / analysis
  • Amylose / chemistry
  • Carbohydrates / analysis
  • Carbohydrates / chemistry*
  • Cellulose / analogs & derivatives
  • Cellulose / analysis
  • Cellulose / chemistry
  • Chemistry, Pharmaceutical / methods
  • Chromatography, High Pressure Liquid / methods
  • Molecular Structure
  • Phenylcarbamates / analysis
  • Phenylcarbamates / chemistry
  • Piperazines / analysis
  • Piperazines / chemistry*
  • Stereoisomerism*

Substances

  • Carbohydrates
  • Phenylcarbamates
  • Piperazines
  • Chiralpak AD
  • Cellulose
  • Amylose