A. U. Isakhanyan, G. Gevorgyan, A. Arakelyan
Sep 19, 2014
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Russian Journal of Organic Chemistry
Abstract
In preceding publications we reported on the synthesis of tertiary aminoalkanols hydrochlorides and some their biologic properties [1–3]. The goal of this study is the search for biologically active compounds in the new series of tertiary aminoalkanols, in particular, the estimation of antibacterial activity of these compounds. The objects of investigation were synthesized along the scheme we had developed. The initial compounds 1-(4-butoxyphenyl)and 1-[4-(3-methylbutoxy)phenyl]-2-phenylethanones I and II were obtained by Friedel–Krafts reaction from phenylacetyl chloride and substituted benzenes [4]. The aminomethylation of compounds I and II with paraformaldehyde and morpholine in ethanol medium (pH 8–9) afforded 1-(4butoxyphenyl)and 1-[4-(3-methylbutoxy)phenyl]-3(morpholin-4-yl)-2-phenylpropan-1-ones III and IV [5]. The subsequent nucleophilic addition of Grignard compounds in dry ether converted the morpholinopropanones into 3-(4-butoxyphenyl)and 3-[4-(3methylbutoxy)phenyl]-1-(morpholin-4-yl)-2-phenylalkan-3-ols Vа–Vj that were transformed into hydrochlorides VIа–VIj by treating with an ether solution of hydrogen chloride [5, 6]. Compounds VIа–VIj are crystalline substances whose structure was confirmed by Н NMR and IR DOI: 10.1134/S1070428014080247