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The Preparation of Lidocaine
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Abstract
In this experiment, which is intended for the introductory organic laboratory, the widely used local anesthetic Lidocaine is synthesized in two steps from 2,6-dimethylaniline. In the first step, the amine is acylated with chloroacetyl chloride. In the second step, the amide is subjected to nucleophilic substitution by diethylamine to give the final product with an overall yield of 71% based on 2,6-dimethylaniline. I have used this experiment in my organic class for several years with excellent results. Average students can isolate the crude product in less than three hours.
Keywords (Audience):
Second-Year UndergraduateKeywords (Domain):
Organic ChemistryKeywords (Subject):
SynthesisCiting Articles
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This article has been cited by 2 ACS Journal articles (2 most recent appear below).
Synthesis of Two Local Anesthetics from Toluene: An Organic Multistep Synthesis in a Project-Oriented Laboratory Course
Patricia Demare and Ignacio ReglaJournal of Chemical Education2012 89 (1), 147-149Synthesis of Two Local Anesthetics from Toluene: An Organic Multistep Synthesis in a Project-Oriented Laboratory Course
Patricia Demare and Ignacio ReglaJournal of Chemical Education2012 89 (1), 147-149This article describes one of the projects in the advanced undergraduate organic chemistry laboratory course concerning the synthesis of two local anesthetic drugs, prilocaine and benzocaine, with a common three-step sequence starting from toluene. ...
The Synthesis and Isolation of N-tert-Butyl-2-phenylsuccinamic Acid and N-tert-Butyl-3-phenylsuccinamic Acid. An Undergraduate Organic Chemistry Laboratory Experiment
Victor Cesare , Ishwar Sadarangani , Janet Rollins and Dennis CostelloJournal of Chemical Education2004 81 (5), 713The Synthesis and Isolation of N-tert-Butyl-2-phenylsuccinamic Acid and N-tert-Butyl-3-phenylsuccinamic Acid. An Undergraduate Organic Chemistry Laboratory Experiment
Victor Cesare , Ishwar Sadarangani , Janet Rollins and Dennis CostelloJournal of Chemical Education2004 81 (5), 713This experiment, which demonstrates that two isomeric products are obtained when an unsymmetrical anhydride is reacted with a nucleophile and that these isomers are easily separated based on their difference in acidity, is useful in introducing the topic ...
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- Received: August 03, 2009
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