An Approach in Synthesis of 1-Morpholino-2-phenylethane-1,2-dione Catalyzed by Copper (II) Bromide

  • Didin Mujahidin Division of Organic Chemistry, Faculty of Mathematics and Natural Sciences, Institut Teknologi Bandung, Indonesia https://orcid.org/0000-0002-6903-8694
  • Wiwin Mujiati Division of Organic Chemistry, Faculty of Mathematics and Natural Sciences, Institut Teknologi Bandung, Indonesia
  • Anita Alni Division of Organic Chemistry, Faculty of Mathematics and Natural Sciences, Institut Teknologi Bandung, Indonesia
Keywords: Amination, Catalysis, Copper (II), α-Ketoamides

Abstract

A novel approach towards synthesis of α-Ketoamides was serendipitously found in acetophenone's reaction with a secondary amine catalyzed by copper (II) bromide. This methodology is a promising simple alternative to access biologically active compounds containing α-Ketoamides. Reactions were carried out at room temperature using dimethyl sulfoxide (DMSO) as solvent and catalyst loading at 10 mol %. The products were purified using a chromatographic method and analyzed extensively by spectroscopic methods, namely 1D (1H and 13C) and 2D NMR (HMBC and HSQC). The reaction of acetophenone and morpholine furnished a yield of 6%. Acetophenone derivatives bearing benzyl and acetyl groups were prepared from para-hydroxy acetophenone with 25% and 99% yields, respectively. The products were analyzed by spectroscopic method, namely 1H and 13C NMR.  The presence of substituents, namely hydroxyl, benzyl, acetyl group, prevent the formation of α-Ketoamides. Formation of α-Ketoamides in this reaction condition was proposed as the result of the oxidation product in the catalytic cycle of Cu (II).

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The reaction of acetophenone and morpholine catalyzed by copper (II) furnished α-Ketoamide. However, substituted acetophenone, namely hydroxyl, acetyl, and benzyl group, did not yield a product when subjected to a similar condition. Mechanism of product formation is under investigation, proposed as oxidation that occurs in one of the Cu (II) catalytic cycle.
Published
2020-12-30
How to Cite
Mujahidin, D., Mujiati, W., & Alni, A. (2020). An Approach in Synthesis of 1-Morpholino-2-phenylethane-1,2-dione Catalyzed by Copper (II) Bromide. Journal of the Indonesian Chemical Society, 3(3), 145. https://doi.org/10.34311/jics.2020.03.3.145