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

ABSTRACT

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.