Synthesis, conformation, and stereodynamics of a salt of 2-{[2-(3,4-dichlorophenyl)- ethyl]propylamino}-1-pyridin-3-ylethanol.
[reaction: see text] 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.
Korosec
Tina
T
Drug Discovery, Lek Pharmaceuticals d. d., Verovskova 57, SI-1526 Ljubljana, Slovenia.
Grdadolnik
Joze
J
Urleb
Uros
U
Kocjan
Darko
D
Grdadolnik
Simona Golic
SG
D000431:Ethanol / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry*; D004983:Ethanolamines / Q000138:chemical synthesis* / Q000737:chemistry*; D007202:Indicators and Reagents; D008958:Models, Molecular; D008968:Molecular Conformation; D010636:Phenols / Q000737:chemistry; D011437:Propylamines / Q000737:chemistry; D011725:Pyridines / Q000138:chemical synthesis* / Q000737:chemistry*
C512156:2-((2-(3,4-dichlorophenyl)ethyl)propylamino)-1-pyridin-3-ylethanol; D004983:Ethanolamines; D007202:Indicators and Reagents; D010636:Phenols; D011437:Propylamines; D011725:Pyridines; D000431:Ethanol