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Communication | Regular issue | Vol 81, No. 11, 2010, pp.2471-2478
Published online, 1st October, 2010
DOI: 10.3987/COM-10-12064
Novel Application of Electrooxidative Method for the Cyclization of N-Benzyl-2-(hydroxymethyl)- and N-Benzyl-2-(2-hydroxyethyl)piperidines

Mitsuhiro Okimoto,* Takashi Yoshida, Masayuki Hoshi, and Kousuke Ohashi

*Department of Biotechnology and Environmental Chemistry, Kitami Institute of Technology, Koen-cho 165, Kitami, Hokkaido 090-8507, Japan

Abstract

Several novel 1,3-oxazinane and oxazolidine derivatives were obtained from the corresponding N-benzyl-2-(2-hydroxyethyl)- and N-benzyl-2-(hydroxymethyl)piperidines via electrochemical oxidation. The reactions were carried out in methanol under basic conditions. The yields of the cyclic products were significantly improved using catalytic amounts of iodide ions, which presumably act as effective electron carriers in the two-electron oxidation process.