Synthesis, characterization and dynamic NMR studies of a novel chalcone based N-substituted morpholine derivative

The synthesis of a novel chalcone based N-substituted morpholine derivative namely, (E)-1-(biphenyl-4-yl)-3-(4-(5-morpholinopentyloxy) phenyl) prop-2-en-1-one (BMPP), using a two step protocol is reported. The compound is characterized by FTIR, GC–MS and FTNMR spectroscopy techniques. Advanced 2D NMR techniques such as gradient enhanced COSY, HSQC, HMBC and NOESY were employed to establish through-bond and through-space correlations. Dynamic NMR measurements were carried out to obtain the energy barrier to ring inversion of the morpholine moiety.

► A novel chalcone based N-substituted morpholine derivative is synthesized. ► Complete assignments of 1H and 13C signals were made using modern 2D NMR techniques. ► The stereo dynamics of the morphline moiety have been examined by dynamic NMR spectroscopy. ► The energy barrier to morphline ring inversion is calculated.