Abstract
Dimethindene is a selective histamine H1 antagonist and is commercially available as a racemate. Upon analyzing the synthetic pathways currently available for the industrial preparation of dimethindene, we set up a sustainable approach for the synthesis of this drug, switching from petroleum-based volatile organic compounds (VOCs) to eco-friendly solvents, such as 2-methyltetrahydrofuran (2-MeTHF) and cyclopentyl methyl ether (CPME) belonging to classes 3 and 2, respectively. Beyond decreasing the environmental impact of the synthesis (E-factor: 24.1–54.9 with VOCs; 12.2–22.1 with 2-MeTHF or CPME), this switch also improved the overall yield of the process (from 10% with VOCs to 21–22% with 2-MeTHF or CPME) and remarkably simplified the manual operations, working under milder conditions. Typical metrics applied at the first and second pass, according to the CHEM21 metrics toolkit, were also calculated for the whole synthetic procedure of dimethindene, and the results were compared with those of the classical procedure.
Funder
Ministero dell’Università e della Ricerca
Subject
Chemistry (miscellaneous),Analytical Chemistry,Organic Chemistry,Physical and Theoretical Chemistry,Molecular Medicine,Drug Discovery,Pharmaceutical Science
Reference35 articles.
1. Why Sustainability is Now the Key Driver of Innovation;Nidumolu;Harv. Bus. Rev.,2009
2. Anastas, P.T., and Warner, J.C. Green Chemistry: Theory and Practice, 2000.
3. The 24 Principles of Green Engineering and Green Chemistry: “IMPROVEMENTS PRODUCTIVELY”;Tang;Green Chem.,2008
4. Allen, D.T., and Shonnard, D.R. Green Engineering: Environmentally Conscious Design of Chemical Processes, 2002.
5. How do you select the “greenest” technology? Development of guidance for the pharmaceutical industry;Jiménez-González;Clean Prod. Process.,2001
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