An NMR Study on Prucalopride

Abstract

4-Amino-5-chloro-2,3-dihydro-N-[1-(3-methoxypropyl)-4-piperidinyl]-7-benzofurancarboxamide was synthesized by amide condensation reaction using 4-amino-5-chloro-2,3-dihydrobenzofuran-7-carboxylic acid and 1-(3-methoxypropyl)- 4-piperidinamine as the reactants. The resultant compound, also named prucalopride, is a derivative of dihydrobenzofuran 5-H4 receptor antagonist, and an important drug for treating chronic constipation. The NMR spectrum of prucalopride is crowded and complex due to the fact that there are many carbon atoms in the molecule have similar chemical environment. In this study, ultra-performance liquid chromatography tandem mass spectrometry (UPLC-MS/MS) and liquid chromatography- high resolution mass spectrometry (LC-HRMS) were used to analyze the composition of prucalopride. 1H NMR, 13C NMR, DEPT, 1H-1H COSY, 1H-13C HSQC and 1H-13C HMBC spectra of the compound were collected, and its 1H and 13C NMR signals were assigned.

Keywords

• liquid-state NMR
• dihydrobenzofuran-carboxamide derivative
• prucalopride
• assignment