Synthesis, Conformation, and Stereodynamics of a Salt of 2-{[2-(3,4-Dichlorophenyl)- ethyl]propylamino}-1-pyridin-3-ylethanol

A novel synthetic route was developed for 2-{[2-(3,4-dichlorophenyl)ethyl]propylamino}-1-pyridin-3-ylethanol (4). A dynamic process due to nitrogen inversion at the central amine nitrogen has been identified by NMR spectroscopy for the dihydrobromide salt of this compound. The conformational propert...

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Veröffentlicht in:	Journal of organic chemistry 2006-01, Vol.71 (2), p.792-795
Hauptverfasser:	Korošec, Tina, Grdadolnik, Jože, Urleb, Uroš, Kocjan, Darko, Grdadolnik, Simona Golič
Format:	Artikel
Sprache:	eng
Schlagworte:	Chemistry Ethanol - analogs & derivatives Ethanol - chemical synthesis Ethanol - chemistry Ethanolamines - chemical synthesis Ethanolamines - chemistry Exact sciences and technology Heterocyclic compounds Heterocyclic compounds with only one n hetero atom and condensed derivatives Indicators and Reagents Models, Molecular Molecular Conformation Organic chemistry Phenols - chemistry Preparations and properties Propylamines - chemistry Pyridines - chemical synthesis Pyridines - chemistry
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Beschreibung
Zusammenfassung:	A novel synthetic route was developed for 2-{[2-(3,4-dichlorophenyl)ethyl]propylamino}-1-pyridin-3-ylethanol (4). A dynamic process due to nitrogen inversion at the central amine nitrogen has been identified by NMR spectroscopy for the dihydrobromide salt of this compound. The conformational properties of the diastereomeric pair were determined by analysis of NOE connectivities and MO calculations.
ISSN:	0022-3263 1520-6904
DOI:	10.1021/jo051455f