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Communication | Regular issue | Vol 19, No. 3, 1982, pp.481-484
Published online, 1st January, 1970
DOI: 10.3987/R-1982-03-0481
2-(2,6-Dimethylpiperidino)acetonitrile as an Acyl Carbanion Equivalent

Takeshi Wakamatsu, Junichi Kondo, Satoshi Hobara, and Yoshio Ban

*Faculty of Pharmaceutical Sciences, Hokkaido University, Kita 12 Nishi 6, Kita-ku, Sapporo, Hokkaido 060-0812, Japan


Reaction of lithio 2-(2,6-dimethylpiperidino)acetonitrile with alkyl halides affords monoalkylation products which are easily hydrolyzed under mild conditions to give the homogeneous aldehyde or its acetal in moderate yield. In the case of alkyl halides having an electron donating group on aromatic ring the cyclization products are obtained.