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Report | Regular issue | Vol 19, No. 9, 1982, pp.1641-1645
Published online, 1st January, 1970
DOI: 10.3987/R-1982-09-1641
The Selectivity in N-Alkylation of Nicotine

Makoto Shibagaki, Hajime Matsushita, Saizo Shibata, Akira Saito, Yasuko Tsujino, and Hajime Kaneko

*Life Science Research Laboratory, Japan Tobacco Inc., 6-2, Umegaoka, Midori-ku, Yokohama, Kanagawa 227-8512, Japan

Abstract

In preference to pyrrolidine, pyridine moiety of nicotine was alkylated by alkyl halides. This preference seemed to result from the difference of steric hinderance around each nitrogen. The reactivity of pyridine moiety was accelerated by the electronic effect of pyrrolidine. The selective alkylation of pyridine appeared to be available for preparation of artificial antigen of nicotine.