Ethylene Glycol → N-BENZYLBENZENE-1,4-DIAMINE

Participants

Reaction Steps

The general procedure under argon was followed using copper(I) iodide (19 mg, 0.10 mmol), K3PO4 (425 mg, 2.00 mmol), benzylamine (218 μL, 2.0 mmol), 4-iodoaniline (219 mg, 1.00 mmol), ethylene glycol (111 μL, 2.00 mmol) and 2-propanol (1.0 mL) at 90° C. Column chromatography using a solvent gradient (hexane/ethyl acetate=2/1 to 1/1, Rf=0.2) afforded 4-(N-benzyl)aminoaniline (101 mg, 51% isolated yield) as brown solid. The spectral data (1H NMR) matched with the literature references and GC analysis indicated >95% purity. See Araki, T.; Tsukube, H. J. Polym. Sci., Polym. Lett. Ed. 1979, 17, 501-505.

Provenance & Evidence