A. U. Isakhanyan, G. Gevorgyan, S. G. Chshmarityan
May 22, 2016
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Journal
Russian Journal of Organic Chemistry
Abstract
We previously reported the synthesis of tertiary aminoalkanol hydrochlorides and some their biological properties [1–3]. The goal of the present work was to find biologically active compounds among a new series of tertiary aminoalkanols, in particular to test them for antitumor activity. As starting compound we used 1-(4-methylphenyl)3-(morpholin-4-yl)-2-phenylpropan-1-one (2) which was prepared by aminomethylation [4] of 1-(4-methylphenyl)-2-phenylethan-1-one (1) with paraformaldehyde and morpholine in ethanol (pH 8–9) [5]. Nucleophilic addition of Grignard reagents to amino ketone 2 in anhydrous diethyl ether afforded the corresponding 1-(4-methylphenyl)-3-(morpholin-4-yl)-2-phenyl-1-Rpropan-1-ols which were converted into hydrochlorides 3a–3p by the action of a solution of HCl in diethyl ether [1–3]. Compounds 3a–3p are crystalline substances whose structure was confirmed by H NMR and IR spectra. The IR spectra of 3a–3p contained an absorption band at 3384–3310 cm due to OH stretching vibrations, while no carbonyl stretching band typical of initial ketone 2 (1655–1680 cm) was observed. The OH proton resonated in the H NMR spectra of 3a–3p as a broadened singlet at δ 5.06–5.95 ppm, and signals from aromatic, alkyl, cyclohexyl, or allyl protons of the R substituent were also present.