Kinetic and equilibrium study of the enantioseparation of paroxetine intermediate on amylose and tartaric acid-based chiral stationary phases.
trans-(-)-Paroxetine is a selective 5-hydroxytryptamine (5-HT) reuptake inhibitor currently used as an antidepressant. trans-(+/-)-3-Ethoxycarbonyl-4-(4'-fluorophenyl)-1-methylpiperidine-2,6-dione is an important intermediate of trans-(-)-paroxetine. It was separated on amylose and tartaric acid-based chiral stationary phases by HPLC. The equilibrium constants and overall mass transfer coefficients together with the axial dispersion coefficients were experimentally determined by moment analysis based on the lumped kinetic model of chromatography. In case of Kromasil CHI-TBB, the equilibrium constants measured were found to be 8.36 and 9.37 for trans-(+) and trans-(-) enantiomers, respectively. For Chiralpak AD-H, the equilibrium constants were 6.68 and 4.13 for trans-(+) and trans-(-) enantiomers, respectively. The axial dispersion coefficients of both enantiomers on Kromasil CHI-TBB column were about one order of magnitude greater than on Chiralpak AD-H. Fast kinetics of mass transfer in both chiral stationary phases was observed. Their overall mass transfer coefficients on Kromasil CHI-TBB and Chiralpak AD-H were 32.12, 33.18, 26.50, 46.85 s(-1) for trans-(+) and trans-(-) enantiomers, respectively. The parameters obtained were utilized to simulate the elution profiles, and the simulated and experimental results match well, which confirmed that the parameters obtained in this study were valid.
Bao
Zongbi
Z
Department of Chemical and Biochemical Engineering, National Laboratory of Secondary Resources Chemical Engineering, Zhejiang University, Hangzhou, China.
Su
Baogen
B
Ren
Qilong
Q
D000688:Amylose / Q000378:metabolism*; D007700:Kinetics; D015394:Molecular Structure; D017374:Paroxetine / Q000737:chemistry* / Q000302:isolation & purification / Q000378:metabolism*; D013237:Stereoisomerism; D013644:Tartrates / Q000737:chemistry*
D013644:Tartrates; D017374:Paroxetine; D000688:Amylose; C029768:tartaric acid