Synthesis of N-[1-(2-Acetyl-4,5-dimethoxyphenyl)propan-2-yl]benzamide and Its Copper(II) Complex

P Marinova; S Nikolova; S Tsoneva

doi:10.1134/S1070363223010218

Synthesis of N-[1-(2-Acetyl-4,5-dimethoxyphenyl)propan-2-yl]benzamide and Its Copper(II) Complex

Russ J Gen Chem. 2023;93(1):161-165. doi: 10.1134/S1070363223010218. Epub 2023 Mar 9.

Authors

P Marinova¹, S Nikolova², S Tsoneva³

Affiliations

¹ Department of General and Inorganic Chemistry with Methodology of Chemistry Education, Faculty of Chemistry, University of Plovdiv, 4000 Plovdiv, Bulgaria.
² Department of Organic Chemistry, Faculty of Chemistry, University of Plovdiv, 4000 Plovdiv, Bulgaria.
³ Department of Analytical Chemistry and Computer Chemistry, University of Plovdiv, 4000 Plovdiv, Bulgaria.

Abstract

This paper represents a convenient method for the synthesis of N-[1-(2-acetyl-4,5-dimethoxyphenyl)propan-2-yl]benzamide and its Cu(II) complex. In silico analysis predicted spasmolytic activity for the compound. Based on the in silico calculations, the importance of the predicted ketoamide, and our previous experiments, we synthesized the ketoamide via ortho-acylation of N-[1-(3,4-dimethoxyphenyl)propan-2-yl]benzamide with acetic anhydride in polyphosphoric acid. We applied the title ketoamide in reaction with Cu(II) varying the solvents. We found that the reaction leads to the formation of a coordination compound when the ligand dissolved in DMSO reacts with a water solution of CuCl₂ in an alkaline environment in a molar ratio M : L : OH^- = 1 : 2 : 2. The structures of the new compounds are discussed based on their melting points, IR, ¹H, ¹³C NMR and Raman spectral data.

Keywords: complexation; copper(II) complexes; in silico prediction; ketoamides.