Reductive amination of 5-acetoxymethylfurfural over Pt/Al₂O₃ catalyst in a flow reactor

Aminomethylhydroxymethylfuran derivatives are well known for their pharmaceutical activities. In this work, the two-step one-pot procedure for the synthesis of N-substituted 5-(acetoxymethyl)-2-furfuryl amines was proposed, which includes two successive reactions: the condensation of 5-acetoxymethylfurfural (AMF) with primary amines and the reduction of obtained imines with hydrogen over supported metal catalysts in a flow reactor. The comparison of the properties of Au, Pd and Pt catalysts in the hydrogenation of imine obtained by reaction of AMF with aniline showed that Pt-based catalysts (both Pt/Al₂O₃ and Pt/C) are highly active and provide high selectivity and stability, while Pd and Au nanoparticles supported on γ-alumina and carbon show low selectivity. A wide range of N-substituted 5-(acetoxymethyl)-2-furfuryl amines was synthesized in good to excellent yields using Pt/Al₂O₃ catalyst and methanol as a solvent.