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Tetraphenylborate Salt of Bambuterol (Bambec®): Synthesis, Characterization and X-ray Structure of N-(2-(3,5-bis((dimethylcarbamoyl)oxy)phenyl)-2-hydroxyethyl)-2-methylpropan-2-aminium tetraphenylborate

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Abstract

The title compound tetraphenylborate salt of bambuterol (Bambec®), N-(2-(3,5-bis((dimethylcarbamoyl)oxy)phenyl)-2-hydroxyethyl)-2-methylpropan-2-aminium tetraphenylborate (4), was prepared in 73 % yield by the reaction of 5-(2-(tert-butylamino)-1-hydroxyethyl)-1,3-phenylene bis(dimethylcarbamate) hydrochloride (bambuterol hydrochloride) (2) with sodium tetraphenylborate (3) in deionized water, at ambient temperature, through anion exchange reaction. The structure of the title borate salt was characterized by IR, mass and 1H NMR analyses. Colorless crystals of 4 suitable for an X-ray structural analysis were obtained by slow evaporation from acetonitrile. Compound 4 crystallizes in the monoclinic, space group P21/c, with a = 8.8931 (2) Å, b = 20.4639 (6) Å, c = 21.4393 (6) Å, β = 93.640 (2)°, V = 3893.81 (18) Å3, Z = 4.

Graphical Abstract

Synthesis, characterization and X-ray structure of tetraphenylborate salt of bambuterol (Bambec®), the drug for the treatment of asthma, bronchospasm, emphysema, and chronic obstructive pulmonary disease.

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Notes

  1. Crystallographic data for the structure 4 has been deposited with the Cambridge Crystallographic Data Center (CCDC) under the numbers CCDC 1037897-1037898. Copies of the data can be obtained, free of charge, on application to CCDC 12 Union Road, Cambridge CB2 1EZ, UK [Fax: +44-1223-336033; e-mail: deposit@ccdc.cam.ac.uk/http://www.ccdc.cam.ac.uk].

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Acknowledgments

The authors would like to extend their sincere appreciation to the Deanship of Scientific Research at King Saud University for its funding of this research through the Research Group Project no. RG-1436-024.

Conflict of interest

The authors have declared that there is no conflict of interest.

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Authors and Affiliations

  1. Department of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, P.O. Box 2457, Riyadh, 11451, Saudi Arabia

    Gamal A. E. Mostafa, Hazem A. Ghabbour, Obaid S. AlRuqi, Hoong-Kun Fun & Hatem A. Abdel-Aziz

  2. X-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia (USM), 11800, Gelugor, Penang, Malaysia

    Hoong-Kun Fun

  3. Department of Applied Organic Chemistry, National Research Center, Dokki, Cairo, 12622, Egypt

    Hatem A. Abdel-Aziz

Authors
  1. Gamal A. E. Mostafa
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  2. Hazem A. Ghabbour
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  3. Obaid S. AlRuqi
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  4. Hoong-Kun Fun
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  5. Hatem A. Abdel-Aziz
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Correspondence to Hatem A. Abdel-Aziz.

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Mostafa, G.A.E., Ghabbour, H.A., AlRuqi, O.S. et al. Tetraphenylborate Salt of Bambuterol (Bambec®): Synthesis, Characterization and X-ray Structure of N-(2-(3,5-bis((dimethylcarbamoyl)oxy)phenyl)-2-hydroxyethyl)-2-methylpropan-2-aminium tetraphenylborate. J Chem Crystallogr 45, 251–256 (2015). https://doi.org/10.1007/s10870-015-0592-0

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  • DOI: https://doi.org/10.1007/s10870-015-0592-0

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