Advanced search
1 file | 1.03 MB Add to list

Continuous-flow multistep synthesis of cinnarizine, cyclizine, and a buclizine derivative from bulk alcohols

(2016) CHEMSUSCHEM. 9(1). p.67-74
Author
Organization
Abstract
Cinnarizine, cyclizine, buclizine, and meclizine belong to a family of antihistamines that resemble each other in terms of a 1-diphenylmethylpiperazine moiety. We present the development of a four-step continuous process to generate the final antihistamines from bulk alcohols as the starting compounds. HCl is used to synthesize the intermediate chlorides in a short reaction time and excellent yields. This methodology offers an excellent way to synthesize intermediates to be used in drug synthesis. Inline separation allows the collection of pure products and their immediate consumption in the following steps. Overall isolated yields for cinnarizine, cyclizine, and a buclizine derivative are 82, 94, and 87%, respectively. The total residence time for the four steps is 90min with a productivity of 2mmolh(-1).
Keywords
alcohols, halogenation, hydrogen chloride, multicomponent reactions, synthesis design, ALKYL CHLORIDES, ORGANIC-SYNTHESIS, PURIFICATION, CHEMISTRY, PRESSURE, SEPARATION

Downloads

  • (...).pdf
    • full text
    • |
    • UGent only
    • |
    • PDF
    • |
    • 1.03 MB

Citation

Please use this url to cite or link to this publication:

MLA
Borukhova, Svetlana, Timothy Noël, and Volker Hessel. “Continuous-flow Multistep Synthesis of Cinnarizine, Cyclizine, and a Buclizine Derivative from Bulk Alcohols.” CHEMSUSCHEM 9.1 (2016): 67–74. Print.
APA
Borukhova, S., Noël, T., & Hessel, V. (2016). Continuous-flow multistep synthesis of cinnarizine, cyclizine, and a buclizine derivative from bulk alcohols. CHEMSUSCHEM, 9(1), 67–74.
Chicago author-date
Borukhova, Svetlana, Timothy Noël, and Volker Hessel. 2016. “Continuous-flow Multistep Synthesis of Cinnarizine, Cyclizine, and a Buclizine Derivative from Bulk Alcohols.” Chemsuschem 9 (1): 67–74.
Chicago author-date (all authors)
Borukhova, Svetlana, Timothy Noël, and Volker Hessel. 2016. “Continuous-flow Multistep Synthesis of Cinnarizine, Cyclizine, and a Buclizine Derivative from Bulk Alcohols.” Chemsuschem 9 (1): 67–74.
Vancouver
1.
Borukhova S, Noël T, Hessel V. Continuous-flow multistep synthesis of cinnarizine, cyclizine, and a buclizine derivative from bulk alcohols. CHEMSUSCHEM. 2016;9(1):67–74.
IEEE
[1]
S. Borukhova, T. Noël, and V. Hessel, “Continuous-flow multistep synthesis of cinnarizine, cyclizine, and a buclizine derivative from bulk alcohols,” CHEMSUSCHEM, vol. 9, no. 1, pp. 67–74, 2016.
@article{7245234,
  abstract     = {Cinnarizine, cyclizine, buclizine, and meclizine belong to a family of antihistamines that resemble each other in terms of a 1-diphenylmethylpiperazine moiety. We present the development of a four-step continuous process to generate the final antihistamines from bulk alcohols as the starting compounds. HCl is used to synthesize the intermediate chlorides in a short reaction time and excellent yields. This methodology offers an excellent way to synthesize intermediates to be used in drug synthesis. Inline separation allows the collection of pure products and their immediate consumption in the following steps. Overall isolated yields for cinnarizine, cyclizine, and a buclizine derivative are 82, 94, and 87%, respectively. The total residence time for the four steps is 90min with a productivity of 2mmolh(-1).},
  author       = {Borukhova, Svetlana and Noël, Timothy and Hessel, Volker},
  issn         = {1864-5631},
  journal      = {CHEMSUSCHEM},
  keywords     = {alcohols,halogenation,hydrogen chloride,multicomponent reactions,synthesis design,ALKYL CHLORIDES,ORGANIC-SYNTHESIS,PURIFICATION,CHEMISTRY,PRESSURE,SEPARATION},
  language     = {eng},
  number       = {1},
  pages        = {67--74},
  title        = {Continuous-flow multistep synthesis of cinnarizine, cyclizine, and a buclizine derivative from bulk alcohols},
  url          = {http://dx.doi.org/10.1002/cssc.201501367},
  volume       = {9},
  year         = {2016},
}

Altmetric
View in Altmetric
Web of Science
Times cited: