Separation of substituted phenylpiperazine derivatives with immobilized polysaccharide-based chiral stationary phases by supercritical and subcritical fluid chromatography

doi:10.5246/jcps.2013.03.035

Abstract

Abstract:

Six newly synthesized racemic 1-(substituted phenyl)-4-[3-(indole-4-yl-oxy)-2-hydroxypropyl]-piperazine 1-6 were successfully resolved by carbon dioxide supercritical fluid chromatography (SFC) on an analytical scale column packed with immobilized polysaccharide-based chiral stationary phases (CSPs). We found that separation on the Chiralpak IA CSP was superior to the other two immobilized CSPs (Chiralpak IB and Chiralpak IC), and isopropanol (IPA) was a superior modifier compared to the other five solvents including ethanol, methanol, tetrahydrofuran, acetonitrile and dichloromethane. The effects of organic modifier composition, back pressure, and column temperature for enantioseparation of all six compounds were studied. Of the physical parameters studied, modifier composition had the greatest impact on retention. Changing temperature generally had less impact on retention but produced the greatest selectivity changes. The optimum condition was found as follows: Chiralpak IA column, column temperature 35 ºC, back pressure 120 bar, 35% IPA containing 0.1% diethylamine (v/v) in mobile phase, flow rate of mobile phase 3.0 mL/min, UV detection 283 nm. Separation of all six racemic compounds was completed within 10 min and excellent resolution was obtained. Thus, SFC was found to be the methodology of choice for resolving the enantiomers of this class of compounds.

Key words: Supercritical fluid chromatography, Immobilized polysaccharide-based chiral stationary phases, Enantiomer resolution, Phenylpiperazine derivatives

CLC Number:

R917

Supporting:

Junjun Huang, Mu Yuan^*. Separation of substituted phenylpiperazine derivatives with immobilized polysaccharide-based chiral stationary phases by supercritical and subcritical fluid chromatography [J]. , DOI: 10.5246/jcps.2013.03.035.

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