N-Benzylethylenediamine → HCID 54538472, compound

Participants

Reaction Steps

N-(Phenylmethyl)ethylene diamine (10.38 g) is added dropwise to a solution of α,α'-dibromo-1,2-benzenediacetic acid dimethyl ester [24 g, described by G. Cignarella and A. Vigevani, Gazz. Chim. Ital., 98, 1474 (1968)] in benzene (600 ml). The mixture is refluxed for 6 hr, cooled and filtered. The filtrate is evaporated and the residue is chromatographed on silica gel using diethyl ether-methanol (9:1). The appropriate fractions are evaporated to give isomer A (5.7 g) of the title compound, nmr (CDCl3) δ3.3(m), 3.8(s), 4.6(d), 4.92(d), 5.30(d) and 7.3-7.8(m). The eluant for the above chromatography is changed to methanol-diethyl ether (3:7) and the appropriate eluate fractions are evaporated to give isomer B (4.1 g) of the title compound, nmr (CDCl3) δ3.3(m), 3.8(s), 4.6(d), 4.92(d), 5.30(d) and 7.3-7.8(m).

Provenance & Evidence