Ethyl bromoacetate → N-ethoxycarbonylmethyl-N-(2-ethoxycarbonylpropyl)benzylamine

Participants

Reaction Steps

88.4 g (0.53 mole) of ethyl bromoacetate were added to a solution of 98.0 g (0.44 mole) of N-(2-ethoxycarbonylpropyl)benzylamine [prepared as described in Step (1) above] dissolved in 200 ml of ethanol, and the mixture was heated under reflux for 2 hours. The reaction mixture was then poured into 500 ml of ice-water and made alkaline by the addition of a 50% w/v aqueous solution of sodium hydroxide. It was then extracted with ethyl acetate. The ethyl acetate extract was washed, in turn, with a 1N aqueous solution of sodium hydroxide and with water and dried. It was then freed from the solvent by evaporation under reduced pressure. The residue was purified by column chromatography through silica gel eluted with a 1:9 by volume mixture of ethyl acetate and toluene, to give 83.0 g of N-ethoxycarbonylmethyl-N-(2-ethoxycarbonylpropyl)benzylamine as a pale yellow oil.

Provenance & Evidence