Reaction Steps
In an analogous manner to example 6, the title compound (0.83 g, recrystallized from 27 mL methanol and 15 mL acetonitrile) as a white solid, mp 265°-270° C. dec., is prepared from ethyl-4-(1-piperazinyl)benzo[b]thiophene-2-carboxylate monohydrochloride (5.5 g, 16.8 mmol, prepared in example 5), 4-fluorophenethyl bromide (3.42 g, 16.8 mmol), sodium bicarbonate (2.83 g, 33.7 mmol) and N,N-dimethylformamide (85 mL); 1H NMR (DMSO-d6) δ 11.33 (1H, bs), 8.10 (1H, s), 7.76 (1H, d, J=8.2 Hz), 7.50 (1H, t, J=7.9 Hz), 7.37 (2H, m), 7.20 (2H, m), 7.08 (1H, d, J=7.6 Hz), 4.37 (2H, q, J=7.1 Hz), 3.69 (2H, m), 3.58 (2H, m), 3.37 (6H, bm), 3.15 (2H, m), 1.34 (3H, t, J=7.1 Hz); 13C NMR (DMSO-d6) δ 162.77, 161.87, 148.21, 142.83, 132.63, 132.00, 130.59, 128.34, 127.83, 118.04, 115.56, 115.27, 113.73, 61.51, 56.16, 51.14, 48.82, 28.46, 14.17; 19F NMR (DMSO-d6) δ-115.65; IR (KBr) 1716, 1512, 1446, 1282, 1246, 754 cm-1 ; CI/MS (CH4) 413(100%). IC50 =7.4 nM (5-HT1ABinding Affinity) IC50 =120 nM (5-HT1DBinding Affinity) pA2 =7.53 (0% ) (blocking of 5-HTl-like-mediated contraction in canine saphenous vein )
