A simple method for <i>N</i>-phenoxyethylation of anilines

We wanted to search for new reaction conditions to prepare the title compounds, to be checked later in novel syntheses of heterocyclic compounds. To the best of our knowledge, there was no report in the literature of any well-established method for the preparation of N-(2-phenoxyethyl)anilines 1.Facultad de Ciencias Exacta

A Simple Method for N-Phenoxyethylation of Anilines

Abstract: We wanted to search for new reaction conditions to prepare the title compounds, to be checked later in novel syntheses of heterocyclic compounds. To the best of our knowledge, there was no report in the literature of any well-established method for the preparation of N-(2-phenoxyethyl)anilines 1. The scarce previously reported preparations involved large excesses of some starting materials, relatively high temperatures and long reaction times [1, 2]. We have recently reported a general procedure for that preparation [3] although at that stage only moderate yields were obtained. We describe here a better and simpler procedure for achieving not only compounds 1 in good yields, but also for extending the scope of the reaction to the synthesis of the related bis-N-(2-phenoxy-ethyl)anilines 2. In order to avoid β-elimination reactions in molecules bearing a phenoxyethyl group, the reaction was carried out precluding strong acidic or basic media, see Scheme. NH