Direct high-performance liquid chromatographic separation of the enantiomers of venlafaxine and 11 analogs using amylose-derived chiral stationary phases.
A direct liquid chromatographic enantioselective separation of venlafaxine and 11 analogs was obtained in the normal phase mode using Chiralpak AD. For some compounds, a comparison between the enantioseparation using coated and immobilized amylose tris(3,5-dimethylphenylcarbamate) chiral stationary phases (Chiralpak AD and Chiralpak IA, respectively) was made. The best separations were achieved on Chiralpak AD with ethanol as alcoholic modifier in a mobile phase made basic by DEA addition: separation factor ranges between 2.08 and 1.15 and resolution factor between 7.0 and 1.0. Using the same CSP and 2-propanol doped with TFA as acidic modifier, 10 compounds were enantioseparated with separation factor ranging between 1.40 and 1.04 and resolution factor between 3.1 and 0.3. The use of ethanol as alcoholic modifier also has the advantage of better solubility of the compounds in the mobile phase. The nature of the substituent (electron donating or withdrawing) affects in general the separation factor. A memory effect that involves a long equilibration time of the CSP is present when switching from an acidic mobile phase to a basic one.
Caccamese
Salvatore
S
Dipartimento di Scienze Chimiche, Università di Catania, Catania, Italy. scaccamese@dipchi.unict.it
Bianca
Salvatore
S
Carter
Guy T
GT
D019840:2-Propanol / Q000737:chemistry; D000688:Amylose / Q000737:chemistry*; D002851:Chromatography, High Pressure Liquid / Q000379:methods*; D003511:Cyclohexanols / Q000737:chemistry* / Q000302:isolation & purification*; D000431:Ethanol / Q000737:chemistry; D006863:Hydrogen-Ion Concentration; D013237:Stereoisomerism; D000069470:Venlafaxine Hydrochloride
D003511:Cyclohexanols; D000431:Ethanol; D000069470:Venlafaxine Hydrochloride; D000688:Amylose; D019840:2-Propanol