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New Toluene Hemi Solvate of the Proton Pump Inhibitor Piperazinium Esomeprazolate

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Abstract

The new toluene hemisolvate of the piperazinium salt of esomeprazole, ((S)-5-methoxy-2-[(4-methoxy-3,5-dimethyl-pyridin-2-yl)methylsulfinyl]-3H-benzimidazole, C17H19N3O3S) has the composition piperazinium esomeprazolate 0.5 toluene. The unit cell has monoclinic P21 symmetry with the cell parameters a = 10.0903(16) Å, b = 16.234(3) Å, c = 15.316(2) Å, β = 92.746(12)°, V = 2,506.0(7) Å3. It contains four piperazinium, four esomeprazolate and two toluene molecules. The crystal structure exhibits intermolecular hydrogens bonds within the layers and Van der Waals contacts between the layers. Additionally, three new crystal phases of solvent-free piperazinium esomeprazolate were found.

Index Abstract

The title compound is a toluene hemisolvate of the piperazinium salt of esomeprazole, ((S)-5-methoxy-2-[(4-methoxy-3,5-dimethyl-pyridin-2-yl)methylsulfinyl]-3H-benzimidazole. Single crystal X-ray diffraction analysis reveals that the molecules crystallize in layers. In a layer the molecules are held together by classical hydrogen bonds whereas the layers on the other hand are connected by vdW contacts.

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Acknowledgement

We thank ratiopharm GmbH, Graf-Arco Str. 3, 89079 Ulm, Germany for supplying piperazinium esomeprazolate, and for financial support; Edith Alig, Institut of Inorganic and Analytical Chemistry, University of Frankfurt, is acknowledged for numerous X-ray powder measurements.

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Authors and Affiliations

  1. Institut für Anorganische Chemie, J. W. Goethe-Universität Frankfurt, Max-von-Laue-Str. 7, 60438, Frankfurt/Main, Germany

    Jürgen Brüning, Michael Bolte & Martin U. Schmidt

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  1. Jürgen Brüning
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  2. Michael Bolte
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  3. Martin U. Schmidt
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Correspondence to Michael Bolte.

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Brüning, J., Bolte, M. & Schmidt, M.U. New Toluene Hemi Solvate of the Proton Pump Inhibitor Piperazinium Esomeprazolate. J Chem Crystallogr 39, 256–260 (2009). https://doi.org/10.1007/s10870-008-9464-1

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  • DOI: https://doi.org/10.1007/s10870-008-9464-1

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