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Synfacts 2009(11): 1296-1296  
DOI: 10.1055/s-0029-1218064
Polymer-Supported Synthesis
© Georg Thieme Verlag Stuttgart ˙ New York

Pd/C-Catalyzed N-Debenzylation of Benzylamines

Contributor(s): Yasuhiro Uozumi, Yoichi M. A. Yamada, Hidetoshi Ohta
C. Cheng, J. Sun, L. Xing, J. Xu, X. Wang*, Y. Hu*
Tsinghua University, Beijing, P. R. of China
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Publication History

Publication Date:
22 October 2009 (online)

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Significance

A new reaction system for the N-debenzylation of benzylamines 1 using Pd/C catalyst and ClCH2CHCl2 (3) directly leading to amine hydrochlorides 2 was developed. The reaction proceeds through the hydrodechlorination of 3, benzylamine˙HCl salt formation, and N-debenzylation (hydrogenolysis). Thus, the reaction of 1 with 3 was carried out in the presence of 10% Pd/C in MeOH under an atmospheric pressure of hydrogen to give the corresponding amine hydrochlorides 2 (18 examples, 94-99% yield).