Publication date: 28 January 2014
Source:Tetrahedron, Volume 70, Issue 4
Author(s): Chuanjie Cheng , Bo Wang , Nan Liu , Wenwen Chen , Xinyan Wang , Yuefei Hu
A novel Pd–C catalytic hydrodechlorination–hydrogenation was developed for a multi-step one-pot transformation of 4-acylpyridines. Under the selected conditions, 4-benzoylpyridines and 4-alkanoylpyridines were chemoselectively converted into the corresponding 4-benzylpiperidine hydrochlorides and α-alkyl-4-piperidinemethanol hydrochlorides, respectively. This catalytic method was performed simply by an addition of 1 equiv of ClCH2CHCl2 to the conventional hydrogenation system and directly gave the crystalline piperidine hydrochlorides in practical quantitative yields.
Graphical abstract