Piperazin-2-ones are a common structural motif found in medicinal chemistry across a wide range of therapeutic areas. Numerous different methods exist for constructing these rings, such as double alkylation of amide precursors with 1,2-dibromoethane or activation followed by intramolecular cyclization of N-(2-hydroxylethyl)-amides. Herein, we describe a convenient approach to form many bi- and tricyclic systems containing the piperazinone moiety 1 via a two-step amide coupling-alkylation process using N-substituted-2-chloro-ethan-1-amine. These compounds can also be transformed to the corresponding piperazines 2 with potential for further manipulations. Additionally, the method disclosed was also broadened to give systems with medium ring sizes.

Synthesis of piperazinone-containing systems via a two-step amidation-intramolecular alkylation with N-substituted-2-chloro-ethan-1-amine

251st National Meeting (2016)

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