A new method for green production of 2-aminomethylpiperidine from bio-renewable 2,5-bis(aminomethyl)furan

Abstract

2-Aminomethylpiperidine is an important organic compound, which is the basic raw material for the synthesis of flecainide acetate. In this paper, a new method for synthesizing 2-aminomethylpiperidine by selective hydrogenolysis of bio-renewable 2,5-bis(aminomethyl)furan was developed. The catalytic performance of Pt catalysts supported on different carriers (including γ-Al₂O₃, ZrO₂, TiO₂, H-ZSM-5) and several commercial hydrogenation catalysts was studied. It was found that the Pt/γ-Al₂O₃ catalyst showed the best performance. The effects of the preparation method, reduction temperature and reaction parameters on the catalytic performance of the Pt/γ-Al₂O₃ catalyst were studied. The results show that good Pt dispersion and more acidic sites favor the reactivity and selectivity of hydrogenolysis. The large size of Pt particles facilitates BAMF hydrogenation. The yield of 2-aminomethylpiperidine reached 72.0% at 140 °C and 1 MPa H₂ in aqueous solution using direct hydrogen at 350 °C to reduce 2 wt% Pt/γ-Al₂O₃ catalyst. In addition, the reaction pathways of selective hydrogenolysis of 2,5-bis(aminomethyl)furan to 2-aminomethylpiperidine were proposed.