High-performance liquid chromatographic resolution of 1-(1,4-benzodioxane-2-formyl)-piperazine enantiomers after chiral derivatization.
Chiral separation of racemic mixtures is of the greatest importance to the pharmaceutical industry, as the isomers of a given racemate may exhibit substantially different pharmacological effects, not to mention possibly differing toxicity behaviour. A novel chiral separation method is developed for the determination of 1-(1,4-benzodioxane-2-formyl)piperazine (BFP) enantiomers. The indirect resolution is performed by applying precolumn derivatization with the chiral reagent 2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyl isothiocyanate (GITC). The resulting diastereoisomers are separated on a reversed-phase ODS column with methanol-potassium dihydrogen phosphate (0.02mol/L, 50:50) as mobile phase. UV detection is at 250 nm. The effect of mobile phase composition upon resolution and analysis time is investigated. Two diastereoisomers show nearly base-line separation under optimal chromatographic conditions. The presented study provides a simple and accurate method for the enantiomeric quality control and the optical purity assay of BFP.
Chen
Zhiqiong
Z
Department of Pharmaceutical Chemistry and Biological Materials, Chongqing Medical University, Chongqing 400016, PR China. chenzhiqiong@sina.com
Yu
Yu
Y
Li
Longjiang
L
D002621:Chemistry / Q000379:methods*; D002845:Chromatography / Q000295:instrumentation / Q000379:methods*; D002851:Chromatography, High Pressure Liquid / Q000379:methods*; D017879:Isothiocyanates / Q000737:chemistry*; D000432:Methanol / Q000032:analysis; D008956:Models, Chemical; D010666:Phenylpropionates / Q000737:chemistry*; D010710:Phosphates / Q000032:analysis; D017680:Potassium Compounds / Q000032:analysis; D013237:Stereoisomerism; D014466:Ultraviolet Rays
D017879:Isothiocyanates; D010666:Phenylpropionates; D010710:Phosphates; D017680:Potassium Compounds; C041943:2,3,4,6-tetra-O-acetylglucopyranosylisothiocyanate; C041630:2-benzyl-3-formylpropanoic acid; C013216:potassium phosphate; D000432:Methanol