Sulfuric Acid → N1,N1-Diallyl-1-[4-(propylsulphonyl)phenyl]ethane-1,2-diamine

Participants

Reaction Steps

Anhydrous THF (5 mL) was cooled to 0° C. and treated with 98% sulphuric acid (0.28 mL, 5.25 mmol). After stirring for 15 mins, lithium aluminium hydride (10.5 mL of 1.0M solution in THF, 10.5 mmol) was added drop wise over 10 mins. The mixture was stirred at 0° C. for 60 minutes before addition of a solution of (diallylamino)[4-(propylsulphonyl)phenyl]acetonitrile (1.22 g, 3.83 mmol) in THF (3+2 mL washing). The mixture was stirred at 0° C. for 30 mins then at 40° C. for 1 h. The reaction was allowed to cool and carefully treated with powdered sodium sulphate decahydrate (3 g). The mixture was stirred at ambient temperature for 15 h, then filtered and the filtrate concentrated to give a pale yellow oil. Used without further purification. 1H NMR (400 MHz, CDCl3) δ 1.01 (3H, t, J=7.4 Hz), 1.75-1.81 (2H, m), 2.82 (2H, dd, J=14.6, 7.6 Hz), 2.95 (1H, dd, J=13.0, 6.0 Hz), 3.06-3.10 (2H, m), 3.18 (1H, dd, J=13.1, 7.5 Hz), 3.28-3.33 (2H, m), 3.86 (1H, br t, J=67 Hz), 5.15-5.20 (4H, m), 5.77-5.85 (2H, m), 7.44 (2H, d, J=8.3 Hz), 7.88 (2H, d, J=8.3 Hz); m/z (ES+) 323 (M+H), 306 (M−NH2).

Provenance & Evidence