Benzocaine → ethyl 4-(4,4-dimethyl-2,6-dioxopiperidin-1-yl)benzoate

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Reaction Steps

A solution of ethyl 4-aminobenzoate (1.0 g, 6.1 mmol) and 3,3-dimethylglutaric anhydride (0.95 g, 6.7 mmol) in 1,2-dichloroethane (15 mL) was heated to reflux for 1 hour, cooled to room temperature, and treated dropwise with acetyl chloride (0.88 mL, 12.5 mmol). The mixture was heated to reflux for 1 hour, cooled to room temperature, diluted with dichloromethane, washed sequentially with water, saturated NaHCO3, and brine, dried (MgSO4), filtered, and concentrated to provide the desired product. MS(DCI(+)) m/e 290 (M+H)+.

Provenance & Evidence