Ethyl cyanoacetate → HCID 408695, compound

Participants

Reaction Steps

A mixture containing 1.05 g (9.27 mmoles) of 1-methyl-4-piperidone (commercially available: Aldrich Chemical Co., 1.00 mL (9.4 mmoles) of ethyl cyanoacetate, and 148 mg of ammonium acetate in 35 mL of benzene was heated at reflux for 3 hours with continuous azeotropic removal of water by means of a Dean-Stark trap. The product was isolated by cooling the mixture to room temperature, pouring it into 30 mL of 2:1 (v/v) 1M aqueous NaOH:saturated brine, and extraction with ether. The organic extracts were washed with 10% aqueous sodium chloride solution, then were dried over anhydrous sodium sulfate and subsequently filtered. Removal of the ether and benzene by evaporation at reduced pressure afforded 1.46 g (76% yield) of cyanoester 9.

Provenance & Evidence