Five new 3-(4-arylpiperazin-1-yl)-2-hydroxypropyl 4-propoxybenzoates were designed and synthesized as potential dual antihypertensive agents. The compounds were prepared as free bases and subsequently transformed to hydrochloride salts. The position of protonation of nitrogen atoms in the piperazine ring of hydrochloride salts was determined by means of (13)C-CP/MAS and (15)N-CP/MAS NMR and IR spectroscopy. Using these solid-state analytical techniques, it was found that both nitrogen atoms were protonated when excess hydrogen chloride was used for preparation of salts. On the other hand, when the equimolar amount of hydrogen chloride was used, piperazine nitrogen substituted by aryl was protonated.

CEITEC Central European Institute of Technology Masaryk University Kamenice 753 5 62500 Brno Czech Republic

Department of Chemical Drugs Faculty of Pharmacy University of Veterinary and Pharmaceutical Sciences Palackeho 1 61242 Brno Czech Republic

Department of Pharmaceutical Chemistry Faculty of Pharmacy Comenius University Odbojarov 10 83232 Bratislava Slovakia

Global Change Research Institute CAS Belidla 986 4a 60300 Brno Czech Republic

Institute of Macromolecular Chemistry Academy of Sciences of the Czech Republic Heyrovsky sq 2 16206 Prague 6 Czech Republic

Zentiva k s U kabelovny 130 10237 Prague 10 Czech Republic

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Synthesis and Determination of Physicochemical Properties of New 3-(4-Arylpiperazin-1-yl)-2-hydroxypropyl 4-Alkoxyethoxybenzoates