Chiral NMR discrimination of the diastereoisomeric salts of the H3-antagonist 2-[3-(1H-imidazol-4-ylmethyl)piperidin-1-yl]-1H-benzimidazole.
Diastereomeric salts with optically pure (S)-alpha-methoxy-alpha-(trifluoromethyl)phenylacetic acid (MTPA) were used to discriminate the enantiomers of the chiral H(3)-antagonist 2-[3-(1H-imidazol-4-ylmethyl)piperidin-1-yl]-1H-benzimidazole. Chemical-shift differences (Delta delta) in NMR spectra strongly depend on solvent and stoichiometric ratio. The better observable differentiation occurred for the proton at the 2-position of the imidazole ring.
Rivara
Mirko
M
Dipartimento Farmaceutico, Università degli Studi di Parma, V.le G.P. Usberti, 27/A, I-43100 Parma, Italy.
Zuliani
Valentina
V
Fantini
Marco
M
Dallaturca
Elisa
E
Mor
Marco
M
D001562:Benzimidazoles / Q000737:chemistry*; D054828:Histamine H3 Antagonists / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy / Q000379:methods* / Q000592:standards; D010880:Piperidines / Q000737:chemistry*; D012015:Reference Standards; D013237:Stereoisomerism
C541828:2-(3-(1H-imidazol-4-ylmethyl)piperidin-1-yl)-1H-benzimidazole; D001562:Benzimidazoles; D054828:Histamine H3 Antagonists; D010880:Piperidines