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

S. Borukhova, T. Noël, V. Hessel

Research output: Contribution to journalArticleAcademicpeer-review

37 Citations (Scopus)
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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 90 min with a productivity of 2 mmol h−1.
Original languageEnglish
Pages (from-to)67-74
JournalChemSusChem
Volume9
Issue number1
DOIs
Publication statusPublished - 9 Dec 2015

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