Summary
A high-performance liquid chromatographic method for the resolution of the enantiomers of a series ofN-alkyl-N-methylanilineN-oxides is reported. The resolutions were achieved using a Chiralcel, OD chiral stationary-phase with a mobile-phase of hexane and ethanol in varying proportions. The chromatographic order of elution of the enantiomers ofN-ethyl-N-methylanilineN-oxide was determined to be (+)-(R) before (−)-(S).
Similar content being viewed by others
References
J. Meisenheimer, Chem. Ber.,41, 3966 (1908).
J. Meisenheimer, Ann., 117 (1911).
J. Meisenheimer, Ann.,428, 252 (1922).
J. Meisenheimer, H. Glawe, H. Greeske, A. Schorning, E. Vieweg, Ann.,449, 188 (1926).
G. Berti, G. Belluci, Tet. Lett.,51, 3853 (1964).
S. Goldberg, F.-L. Lam, J. Am. Chem. Soc.,91, 5113 (1969).
F. Toda, K. Mori, Z. Stein, I. Goldberg, Tet. Lett.,30, 1841 (1978).
B. Lindeke, A. M. Weli, J. Hermansson, ISSX 2nd European Symposium on Foreign Compound Metabolism (Frankfurt-am-Main), Abstract C17, (1987).
J. W. Gorrod, D. J. Temple, A. H. Beckett, Xenobiotica,9, 17 (1979).
B. Testa, P. Jenner, A. H. Beckett, J. W. Gorrod, Xenobiotica,6, 553 (1976).
D. M. Ziegler, D. Jollow, D. E. Cook, in “Flavins and Flavoproteins”, H. Kamin, Ed., Butterworth and Co., London, 1971, p. 507.
L. A. Damani, W. F. Pool, P. A. Crooks, R. K. Kaderlik, D. M. Ziegler, Molec. Pharmacol.,33, 702 (1988).
G. Aislaitner, L. A. Damani, J. W. Gorrod, Med. Sci. Res.,20, 885 (1992).
J. C. Craig, K. K. Purushothaman, J. Org. Chem.,35, 1721 (1970).
D. A. Cowan, L. H. Patterson, L. A. Damani, J. W. Gorrod, Biomed. Mass Spectrom.,9, 233 (1982).
I. W. Wainer, M. C. Alembik, J. Chromatogr.,358, 85 (1986).
C. Hansch, A. Leo, in “Substituent, Constants for Correlation Analysis in Chemistry and Biology”, J. Wiley and Sons, New York, 1979, p. 50.
M. R. Hadley, H. G. Oldham, P. Camilleri, J. Murphy, A. J. Hutt, L. A. Damani, Biochem. Pharmacol.,45, 1739 (1993).
L. A. Damani, in “Metabolism of Xenobiotics”, J. W. Gorrod, H. Oelschlager and J. Caldwell, Eds., Taylor and Francis, London, 1988, p. 59.
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Hadley, M.R., Damani, L.A., Hutt, A.J. et al. Enantiomeric resolution ofN-alkyl-N-methylanilineN-oxides by high-performance liquid chromatography. Chromatographia 37, 487–491 (1993). https://doi.org/10.1007/BF02275784
Received:
Accepted:
Issue Date:
DOI: https://doi.org/10.1007/BF02275784