Chiral Separation Of Nipecotic Acid Amides
Abstract
1-Decyl-3-(N,N-diethylcarbamoyl)piperidine (1) and α,α′-bis[3-(N-benzyl-N-methylcarbamoyl)piperidinol]-p-xylene (2) represent mono-N-substituted and bis-N-substituted carbamoylpiperidines, or nipecotic acid amides, respectively. Initially, several attempts were made to resolve these compounds using β-cyclodextrin, cellulose carbamate and Pirkle-type columns. However, the interactions of the stereoisomers of the two compounds with these stationary phases did not differ enough to permit satisfactory separations. Baseline resolution was achieved using an α1-acid glycoprotein (AGP) chiral column. The mobile phase was phosphate buffer (pH 7.0). Tetrabutylammonium (TBA) was used as the cationic modifier and ethanol as the unchanged modifier. Circular dichroism was used to identify the enantiomers. Compound 1 was resolved into positive and negative enantiomers and 2 into positive and negative enantiomers and a meso diastereomer. The influence of pH, buffer ionic strength, cationic and unchanged modifier concentrations on retention, chiral selectivity and resolution were evaluated. Based on the results, it is suggested that both ionic and hydrophobic interactions may be responsible for retention and resolution. © 1992.
Recommended Citation
Z. Feng et al., "Chiral Separation Of Nipecotic Acid Amides," Journal of Chromatography A, vol. 609, no. 1 thru 2, pp. 187 - 193, Elsevier, Sep 1992.
The definitive version is available at https://doi.org/10.1016/0021-9673(92)80162-N
Department(s)
Chemistry
International Standard Serial Number (ISSN)
0021-9673
Document Type
Article - Journal
Document Version
Citation
File Type
text
Language(s)
English
Rights
© 2023 Elsevier, All rights reserved.
Publication Date
18 Sep 1992
PubMed ID
1430044
Comments
National Heart, Lung, and Blood Institute, Grant R01HL022236