Benzocaine → Ethyl 4-[3-(1-naphthyloxy)propylamino]benzoate

Participants

Reaction Steps

A solution of 10 g. 3-(α-naphthyloxy)propyl bromide and 12.5 g. ethyl 4-aminobenzoate in 100 ml. hexamethylphosphoramide is stirred at 110° for 15 hours. The cooled solution is diluted with 200 ml. water and extracted 3 times with 100 ml. portions of ether. The combined extracts are washed with brine, dried and evaporated to an orange residue. The product is crystallized from ethanol to yield a solid which is crystallized from ethanol to yield white crystals, m.p. 93°-94° C.

Provenance & Evidence