Ethylene Glycol → Ethyl 4-(benzylamino)benzoate

Participants

Reaction Steps

The general procedure under argon was followed using copper(I) iodide (10 mg, 0.05 mmol), K3PO4 (425 mg, 2.00 mmol), benzylamine (131 μL, 1.20 mmol), ethyl 4-iodobenzoate (167 μl, 1.00 mmol), ethylene glycol (111 μL, 2.00 mmol) and ethanol (1.0 mL). Column chromatography using a solvent mixture (hexane/ethyl acetate 5/1, Rf=0.4) afforded ethyl 4-(N-benzyl)aminobenzoate (113 mg, 50% isolated yield) as light yellow solid. The spectral data (1H NMR) matched with the literature references and GC analysis indicated >95% purity. See Albright, J. D.; DeVries, V. G.; Largis, E. E.; Miner, T. G. Reich, M. F.; Schaffer, S.; Shepherd, R. G.; Upeslacis, J. J. Med. Chem. 1983, 26, 1378-1393; and Onaka, M.; Umezono, A.; Kawai, M.; Izumi, Y. J. Chem. Soc., Chem. Commun. 1985, 1202-1203.

Provenance & Evidence