Sodium Iodide → HCID 19389035, compound

Participants

Reaction Steps

A mixture of 5.5 g (0.015 mol) of 3-(octadecyloxy)benzenamine, 7.3 ml (0.046 mol) of benzyl bromoacetate, 8.2 g (0.038 mol) of 1,8-bis(dimethylamino)naphthalene, 0.64 g (4.26 mmol) of sodium iodide in 100 ml of anhydrous acetonitrile and 25 ml of anhydrous DMF was stirred at reflux under an argon atmosphere for 48 hours. The solvents were removed at reduced pressure and the residue was dissolved in ethyl acetate and washed with 0.05N HCl, with saturated NaHCO3 solution dried and concentrated at reduced pressure. Purification by HPLC using 15% ethyl acetate-hexane gave, after recrystallization of the combined pure fractions from ether-hexane, 6.56 g (69% yield, mp 55°-57°) of N-[3-(octadecyloxy)phenyl]-N-[2-oxo-2-(phenylmethoxy)ethyl]glycine phenylmethyl ester.

Provenance & Evidence