(3-Bromopropyl)benzene → HCID 67619730, compound

Participants

Reaction Steps

In an analogous manner to example 6, the title compound (0.99 g) as a tan solid, mp 210.5°-213° C., is prepared from ethyl-4-(1-piperazinyl)-benzo[b]thiophene-2-carboxylate monohydrochloride (2.40 g, 8.27 mmol, prepared in example 5), dry dimethyl sulfoxide (45 mL), 1-bromo-3-phenylpropane (1.20 mL, 8.27 mmol) and sodium bicarbonate (0.69 g, 8.27 mmol). Recrystallize the title compound from warm methanol (10 mL); 1H NMR (DMSO-d6) δ 11.05 (bs), 7.76 (1H, d, J=8.2 Hz), 7.49 (1H, t, J=7.9 Hz), 7.28 (5H, m), 7.06 (1H, d, J=7.6 Hz), 4.37 (2H, q, J=7.2 Hz) 3.62 (2H, bd), 3.53 (2H, bd), 3.32 (4H, m), 3.18 (2H, m), 2.69 (2H, m), 1.34 (3H, t, J=7.1 Hz); 13C NMR (DMSO-d6) δ 161.86, 148.25, 142.82, 140.49, 132.62, 131.96, 128.41, 128.33, 128.23, 127.86, 126.11, 117.96, 113.65, 61.49, 55.24, 51.03, 48.76, 32.07, 24.71, 14.16; IR (KBr) 2970, 1709, 1284, 1258 cm-1 ; CI/MS (CH4) 409(100%), 408(75%). IC50 =239 nM (5HT1ABinding Affinity) IC50 =551 nM (5HT1DBinding Affinity)

Provenance & Evidence