Synthesis and Characterization of New 3-(4-Arylpiperazin-1-yl)-2-hydroxypropyl 4-Propoxybenzoates and Their Hydrochloride Salts

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Authors	MARVANOVÁ Pavlína PADRTOVÁ Tereza PEKÁREK Tomáš BRUS Jiří CZERNEK Jiří MOKRÝ Petr HUMPA Otakar ORAVEC Michal JAMPILEK Josef
Year of publication	2016
Type	Article in Periodical
Magazine / Source	Molecules
MU Faculty or unit	Central European Institute of Technology
Citation
Web	http://www.mdpi.com/1420-3049/21/6/707/htm
Doi	http://dx.doi.org/10.3390/molecules21060707
Field	Organic chemistry
Keywords	arylcarbonyloxyaminopropanols; phenylpiperazines; synthesis; CP/MASNMR spectroscopy; IR spectroscopy; principle components analysis
Description	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 C-13-CP/MAS and N-15-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.
Related projects:	CEITEC - open access