1-Chloroethyl chloroformate → HCID 19919599, compound

Participants

Reaction Steps

Dissolve ethyl-4-[4-(phenylmethyl)-1-piperazinyl]-benzo[b]thiophene-2-carboxylate (2.00 g, 5.26 mmol, prepared in example 1) in 1,2-dichloroethane (40 mL) under an atmosphere of nitrogen and cool the solution with an ice bath. Add 1-chloroethyl chloroformate (1.40 mL, 13.1 mmol) and warm the reaction to room temperature (20° C.). Stir for 30 minutes and then heat the reaction to reflux for 4.5 hours. After cooling, concentrate under vacuum, add ethanol (40 mL) to the residue, reflux for 1.5 hours under nitrogen and then stir at room temperature for 15 hours. Concentrate under vacuum and recrystallize the residue from warm ethanol (50 mL). Collect the product by suction filtration and wash with ether to provide the title compound (1.14 g) as a white solid, mp 238°-240° C.; 1H NMR (DMSO-d6) δ 9.43 (2H, bs), 8.13 (1H, s), 7.75 (1H, d, J=8.2 Hz), 7.49 (1H, t, J=7.9 Hz), 7.06 (1H, d, J=7.5 Hz), 4.37 (2H, q, J=7.1 Hz), 3.34 (8H, bs), 1.35 (3H, t, J=7.1 Hz); 13C NMR (DMSO-d6) δ 161.90, 148.81, 142.84, 132.69, 131.91, 128.35, 128.01, 117.91, 113.64, 61.50, 48.88, 43.01, 14.17; IR (KBr) 1711, 1281, 1246, 756 cm-1 ; EI/MS (70eV) 290(55%), 248(100%). IC50 =89 nM (5HT1ABinding Affinity) IC50 =47 nM (5HT1DBinding Affinity)

Provenance & Evidence