Four step total synthesis of an H3 receptor antagonist using only tools found in a typical teaching laboratory

Journal article

Organic synthesis in a modern research laboratory uses state-of-the-art equipment to provide inert atmospheres, track reaction progress, and facilitate the purification of intermediates. Such facilities are not available in a high school laboratory. In this paper, synthetic organic chemistry is taken back to basics: A four step total synthesis of a potential histamine H3 receptor antagonist is completed by A-level students in a school laboratory using only basic equipment. In addition to its bioactivity, the target molecule was selected on the basis of its potentially crystalline nature, allowing for the purification of intermediates by recrystallization. A synthetic route was developed that could be conducted without the need for inert conditions and with intermediates stable enough to be left from one week to the next, with characterization of intermediates and the target compound carried out by collaboration with researchers and analytical facilities at the University of Oxford (U.K.). By working on the project, students not only developed their practical chemistry and problem solving skills, but also experienced the thrill of discovery that inspires people to be scientists.

Authors: Smith, C; Mansfield, S; Anderson, E; Burton, J

• Publication status: Published
• Peer review status: Peer reviewed
• Publisher: American Chemical Society
• Journal: Journal of Chemical Education
• Volume: 96
• Issue: 1
• Pages: 137-142
• Publication date: 2018-12-14
• Acceptance date: 2018-11-20
• DOI: 10.1021/acs.jchemed.7b00982
• EISSN: 1938-1328
• ISSN: 0021-9584
• Keywords: hands-on learning/manipulatives; first-year undergraduate/general; synthesis; aromatic compounds; high school/introductory chemistry; medicinal chemistry; organic chemistry; laboratory instruction