A new undergraduate organic laboratory experiment has been developed and implemented for the Ugi 4-component synthesis of the topical anesthetic lidocaine. Paraformaldehyde, diethylamine, and 2,6-dimethylphenyl isocyanide were combined and conveniently stirred at room temperature for a week in methanol with acetic acid. Students successfully collected their product by precipitation and filtration, then characterized it by NMR (1H, 13C, COSY, DEPT, HSQC), IR, MS, and melting point. Students also evaluated three lidocaine synthesis procedures using green chemistry principles and explored the reaction mechanisms of both traditional (N-acylation then N-alkylation) and multicomponent lidocaine syntheses. A comprehensive experimental analysis worksheet was created for remote instruction.

Multicomponent synthesis of lidocaine in an organic laboratory course

ACS Spring 2022

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.