Fentanyl and Its Analogue N-(1-Phenylpyrazol-3-yl)-N-[1-(2-phenylethyl)-4-piperidyl]propanamide: ^1H- and ^<13>C-NMR Spectroscopy, X-Ray Crystallography, and Theoretical Calculations

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The oxalate salts and free bases of fentanyl and N-[1-(2-phenylethyI)-4-piperidyl]-N-(1-phenyl-4-pyrazolyl)propanamide, a new lead compound for long-acting analgesia, have been characterized by 'H- and 13C-NMR spectroscopy. The crystal structure of the hydrochloride of N-[1-(2-phenylethyl)-4-piperidyl]-N-(1-phenyl-4-pyrazolyl)propanamide monohydrate has been determined. Two centrosymmetrically related cations, joined through C(phenyl)-H…π contacts, encapsulate a large void that contains pairs of anions and bridged water molecules into a zero-dimensional (OD) supramolecular motif. The cations are linked to this framework via N^+H…Cl^- contacts. GIAO/B3LYP calculations have been carried out to compare the experimental ^<13>C chemical shifts with the absolute shieldings thus calculated. The protonation of both molecules takes place on the piperidine ring (axial protonation), as has been verified both in the solid state (X-ray) and in solution (NMR).
公益社団法人日本薬学会の論文
2003-08-01