Synthesis of 2-Arylethylamines by the Curtius Rearrangement

Abstract

2-Arylethylamine derivatives were synthesized using the Curtius reaction and with three different methods of preparing the acyl azide functional group. Carbamates derived from isocyanate were convenient protecting groups for alkylation of amines. Starting from benzaldehyde, amphetamine was prepared in three steps through an oxazolidin-2-one intermediate in 62% overall yield.

Keywords:

• Curtius rearrangement
• isocyanate
• oxazolidin-2-one
• potassium tert-butoxide

ACKNOWLEDGMENT

The financial support of the National Institute on Drug Abuse is gratefully acknowledged.