A variety of products from a “simple” reaction of [1-(6-acetyl-2-naphthyl)piperidin-4-yl]methyl 4-methylbenzenesulfonate with nucleophiles in DMF–K2CO3

Abstract

The course of the reaction between [1-(6-acetyl-2-naphthyl)piperidin-4-yl]methyl 4-methylbenzenesulfonate (1) and pyrrolidine, a model nucleophile, in DMF in the presence of anhydrous potassium carbonate at ambient and elevated temperatures is investigated. At elevated temperatures a 1-azabicyclo[2.2.1]heptane derivative is identified as the intermediate in the piperidine-to-pyrrolidine ring contraction process. The formation of formate, carbamate, and hydroxy derivatives, as a consequence of DMF and K₂CO₃ participating in the reaction, is documented.