SYNTHESIS AND REACTIVITY OF SOME MANNICH BASES. IV. QUATERNARY AMMONIUM IODIDES FROM MANNICH BASES OXIMES
Irina Popovici1, Eugenia Comanita2, Gheorghe Roman3 and Bogdan Comanita4
1 "Gr. T. Popa" University of Medicine and Pharmacy, 16 University St., 6600 Iaºi, Romania
2 Department of Organic Chemistry, "Gh. Asachi" Technical University, 71A, Dimitrie Mangeron Blvd., 6600 Iaºi, Romania
3 Chemistry Department, "Transilvania" University, 29 Eroilor Blvd., 2200 Braºov, Romania
4 National Research Council of Canada, Institute for Chemical Process and Environmental Technology, Montreal Road Campus, K1A 0R6, Ottawa, Ontario, Canada
A series of oximes derived from some Mannich bases was transformed at into quaternary ammonium salts at the amine nitrogen atom. The reaction was accomplished on oximes generated from 1-(2'-hydroxy-5'-methylphenyl)-3-dialkylamino-1-propanone and its 4'-methyl-phenyl substituted isomer. Quaternization was performed with methyl iodide in tetrahydrofuran (THF) as well as in ethanol, at room temperature. The structure of the oximes' methiodides was investigated by IR, 1H-NMR, 13C-NMR and FAB spectra.