1,4-Dibromobutane → HCID 67275763, compound

Participants

Reaction Steps

N1,N1-Diallyl-1-[4-(propylsulphonyl)phenyl]ethane-1,2-diamine (445 mg, 1.38 mmol), 1,4-dibromobutane (0.18 mL, 1.51 mmol) and sodium hydrogencarbonate (0.26 g, 3.09 mmol) were heated in toluene at reflux for 17 h. The reaction mixture was allowed to cool to ambient temperature, filtered through Celite and the filter cake washed with ethyl acetate. The filtrate was washed with water and then brine before being dried (MgSO4) and concentrated. The crude product was purified using an SCX cartridge eluting with dichloromethane, then methanol and finally 2M ammonia in methanol to give the title compound as a pale yellow oil (266 mg, 51% yield). 1H NMR (400 MHz, CDCl3) δ 1.00 (3H, t, J=7.5 Hz), 1.69-1.80 (6H, m), 2.45-2.54 (4H, m), 2.83-3.00 (4H, m), 3.05-3.09 (2H, m), 3.21 (2H, dd, J=14.4, 6.0 Hz), 4.07 (1H, dd, J=8.3, 5.2 Hz), 5.11-5.19 (4H, m), 5.76-5.84 (2H, m), 7.58 (2H, d, J=8.3 Hz), 7.83 (2H, d, J=8.4 Hz); m/z (ES+) 377 (M+H), 280 (M−N[allyl]2).

Provenance & Evidence