Α-Eucaine

α-Eucaine is a drug that was previously used as a local anesthetic. It was designed as an analog (chemistry)|analog] of cocaine and was one of the first synthetic chemical compounds to find general use as an anesthetic.

Synthesis

The aldol condensation between two equivalents of acetone gives mesityl oxide, with isophorone as a side-product of this reaction. Ammonolysis of mesityl oxide formed diacetonamine. The reaction of this product with acetone then gives triacetonamine. N-Methylation of the secondary amine gives 1,2,2,6,6-pentamethylpiperidin-4-one. Cyanohydrin formation gives. Esterification of the tertiary alcohol with benzoyl chloride gives. Pinner reaction of the nitrile with acidified ethanol affords alpha-eucaine.