HCID 15289966, compound → HCID 19919614, compound

Participants

Reaction Steps

In an analogous manner to example 2, the title compound (0.89 g) as a white solid, mp 248°-249° C. dec., is prepared from ethyl-4-[4-[2-(4-chlorophenyl)ethyl]-1-piperazinyl]-benzo[b]thiophene-2-carboxylate (1.20 g, 2.80 mmol, prepared in example 18) and lithium aluminum hydride (0.21 g, 5.6 mmol). The title compound is recrystallized from methanol (25 mL) and acetonitrile (10 mL); 1H NMR (CD3OD) δ 7.58 (1H, d, J=8.8 Hz), 7.37 (5H, m), 7.28 (1H, t, J=7.9 Hz), 7.00 (1H, d, J=7.8 Hz), 4.87 (2H, s), 4.07 (9H, m), 3.15 (3H, m); 13C NMR (CD3OD) δ 147.91, 147.51, 143.38, 136.81, 135.92, 134.81, 132.01, 130.62, 126.45, 119.92, 119.85, 114.46, 61.25, 59.20, 54.33, 51.01, 31.17; IR (KBr) 3319, 2584, 1462, 1446, 958, 779 cm-1 ; CI/MS 387(100%). IC50 =2 nM (5HT1ABinding Affinity) IC50 =10 nM (5HT1DBinding Affinity)

Provenance & Evidence