Diethylamine → HCID 15057236, compound

Participants

Reaction Steps

To a solution of 38.1 g (0.52 mol) of diethylamine in 80 mL of toluene and cooled in an ice bath to 0° C. add dropwise a solution of 65.0 g (0.26 mol) of 2-bromoacetonaphthone in 300 mL of toluene. Stir the reaction mixture overnight. Monitor the progress of the reaction by thin-layer chromatography on silica gel (ethyl acetate:hexane, 1:1). Extract the reaction mixture with 3×150 mL of 3N HCl. Adjust the pH of the combined aqueous layers to pH=10 with 50% sodium hydroxide then extract with 3×150 mL of methylene chloride. Combine the extracts and dry over sodium sulfate. Remove the solvent in vacuo, and chromatograph the resultant oil on 2200 g of silica gel, eluting initially with methylene chloride and later with ethyl acetate. Combine the fractions containing product and remove the solvent in vacuo to obtain the title compound.

Provenance & Evidence