Potassium Iodide → 2-{1-[4-(4-Bromo-benzenesulfonyl)-piperazin-1-yl]-ethyl}-quinazoline

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-(1-Bromo-ethyl)-quinazoline (43 mg, 0.18 mmol) and 1-(4-Bromo-benzenesulfonyl)-piperazine (67 mg, 0.22 mmol), potassium iodide (30 g, 0.18 mmol) and potassium carbonate (37 mg, 0.27 mmol) in acetonitrile (1 mL) was heated at 65° C. for 1 day. The reaction mixture was then concentrated in vacuo. The residue was dissolved in dichloromethane and washed with saturated sodium thiosulphate solution, saturated sodium bicarbonate solution and then with water. The organic layer was dried over magnesium sulfate and concentrated in vacuo. The crude product was dissolved in DMSO and purified by HPLC. 1H NMR (400 MHz, CDCl3) δ 9.45 (s, 1H), 8.06 (m, 3H), 7.80 (t, J=7.9 Hz, 1H), 7.72 (d, J=8.5 Hz, 2H), 7.58 (d, J=8.5 Hz, 2H), 4.86 (q, J=7.0 Hz, 1H), 3.65 (m, 2H), 3.43 (m, 6H), 1.88 (d, J=7.0 Hz, 3H) HPLC ret. time 2.45 min, 10-99% CH3CN, 5 min run; ESI-MS m/z 461.1 (M+1)+.

Provenance & Evidence