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Resolution of a Diasteromeric Salt of Citalopram by Multistage Crystallization

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Lorenz,  Heike
Physical and Chemical Foundations of Process Engineering, Max Planck Institute for Dynamics of Complex Technical Systems, Max Planck Society;

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Seidel-Morgenstern,  Andreas
Physical and Chemical Foundations of Process Engineering, Max Planck Institute for Dynamics of Complex Technical Systems, Max Planck Society;
Otto-von-Guericke-Universität Magdeburg, External Organizations;

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Citation

Balawejder, M., Kiwala, D., Lorenz, H., Seidel-Morgenstern, A., Piatkowski, W., & Antos, D. (2012). Resolution of a Diasteromeric Salt of Citalopram by Multistage Crystallization. Crystal Growth & Design, 12(5), 2557-2566. doi:10.1021/cg300166g.


Cite as: http://hdl.handle.net/11858/00-001M-0000-0013-8A02-2
Abstract
Multistage crystallization has been used for resolution of the racemic mixture of citalopram to obtain pure S-citalopram. The racemate was converted to a diasteromeric salt pair using (+)-O,O′-di-p-toluoyl-d-tartaric acid, (+)DTT, as a resolving agent. The obtained salts involved solid solutions almost within the entire range of the crystalline phase composition, which excluded the possibility of a single-stage resolution. Therefore, a multistep crystallization technique was employed that allowed enrichment of the racemate with the desired diastereomer in the liquid phase. Moreover, a procedure for restoring the 1:1 composition of the depleted solid phase has been developed. The procedure was based on formation of a diasteromeric salt pair with the opposite enantiomer of the resolving agent, i.e., (−)DTT. Copyright © 2012 American Chemical Society