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

• Published in: Journal of organic chemistry Vol. 71; no. 2; pp. 792 - 795
• Main Authors: Korošec, Tina, Grdadolnik, Jože, Urleb, Uroš, Kocjan, Darko, Grdadolnik, Simona Golič
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 20.01.2006; Amer Chemical Soc
• Subjects: Chemistry; Chemistry, Organic; 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; Physical Sciences; Preparations and properties; Propylamines - chemistry; Pyridines - chemical synthesis; Pyridines - chemistry; Science & Technology; Chemical synthesis; Nitrogen heterocycle; Conformation; Pyridine derivatives
• ISSN: 0022-3263; 1520-6904
• DOI: 10.1021/jo051455f

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.