1-(2-Bromoethyl)-4-chlorobenzene → HCID 67620121, compound

Participants

Reaction Steps

In an analogous manner to example 6, the title compound (0.56 g) as a white solid, mp 263°-266° C. dec. is prepared from ethyl-4-(1-piperazinyl)benzo[b]thiophene-2-carboxylate monohydrochloride (4.63 g, 14.2 mmol, prepared in example 5), 4-chlorophenethyl bromide (3.27 g, 14.9 mmol), sodium bicarbonate (2.44 g, 29.1 mmol) and anhydrous dimethyl sulfoxide (75 mL). The title compound is recrystallized from methanol (35 mL) and acetonitrile (35 mL); 1H NMR (DMSO-d6) δ 10.76 (1H, s), 8.10 (1H, s), 7.77 (1H, d, J=8.0 Hz), 7.44 (5H, m), 7.08 (1H, d, J=7.8 Hz), 4.37 (2H, q, J=7.0 Hz), 3.64 (4H, m), 3.56 (8H, m), 3.13 (2H, m), 1.34 (3 H, t, J=7.1 Hz); 13C NMR (DMSO-d6) δ 162.42, 151.71, 143.15, 132.82, 130.94, 128.95, 128.86, 128.63, 128.34, 117.59, 113.66, 113.59, 61.97, 52.66, 51.40, 31.20, 24.06, 14.47; IR (KBr) 1714, 1448, 1282, 1246, 754 cm-1 ; CI/MS (CH4) 429(100%). IC50 =53 nM (5HT1ABinding Affinity) IC50 =411 nM (5HT1DBinding Affinity) pA2 =6.51 (blocking of 5-HTl-like-mediated contraction in canine saphenous vein)

Provenance & Evidence