N-Ethylethylenediamine → HCID 52951820, compound

Participants

Reaction Steps

To a solution of compound 35 (4.60 g, 17.5 mmol) in anhydrous tetrahydrofuran (185 mL) was added, under argon, N-ethylethylenediamine (1.80 mL, 17.5 mmol). The mixture was stirred at room temperature for 24 h. The solvent was evaporated under vacuum and the residue was suspended in dichloromethane (95 mL). A 1.0 N aqueous sodium hydroxide solution (140 mL) was added to the mixture. The solution was decanted and the aqueous layer was extracted with dichloromethane (6×120 mL). The organic layers were combined, dried on magnesium sulfate, filtered and evaporated under reduced pressure. The residue was chromatographed (Al2O3, CH2Cl2/EtOH, 98/2, v/v) to give compound 36 (3.37 g, 15.9 mmol) as a yellow solid. Yield 91%; Rf (Al2O3, CH2Cl2/EtOH, 98/2, v/v) 0.16; mp 51-52° C.; IR (KBr) ν 1300, 1416, 1554, 1675, 2700-3050, 3100-3600 cm−1; 1H NMR (200 MHz, CDCl3) δ 1.07 (t, 3H, J=7.1 Hz), 2.63 (q, 2H, J=7.1 Hz), 2.76 (se, 1H), 2.83 (t, 2H, J=5.8 Hz), 3.50 (m, 2H), 7.33 (s, 1H), 7.54 (m, 1H), 7.74 (se, 1H), 8.24 (d, 1H, J=5.1 Hz); MS m/z 212 (M+H+, 1), 124 (8), 96 (15), 71 (19), 58 (100).

Provenance & Evidence