Favorskii-Like Rearrangement of an Aliphatic α-Halo Amide

Abstract

The reaction of the α-bromoamide 2a with 1-cyclopentylpiperazine gives the Favorskii-like rearranged product 4 when the reaction is heated to 70 °C in a mixture of aqueous potassium hydroxide and ethanol. However, when solid sodium carbonate/potassium iodide is used in ethanol, the nonrearranged product 3a is formed instead.

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GRAPHICAL ABSTRACT

Keywords:

• Amino amide
• α-bromoamide
• Favorskii-like rearrangement
• neuroprotective
• neurotrophic

ACKNOWLEDGMENTS

The authors thank Andrew Norbury and Mark Ruston at Peakdale Molecular for preparing compound 4 via the route in Scheme 3; Anette Andersen at the Department of Chemistry, Copenhagen University, for running the HRMS; Brian Kreiser at Niels Clauson-Kaas A/S for running the LC/MS; and Knud J. Jensen at Faculty of Life Sciences, Copenhagen University, for helpful discussions.