Ammonium Chloride → HCID 19919594, compound

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Reaction Steps

In an analogous manner to example 3, the title compound (0.28 g) as a white solid, mp 260.5°-264.0° C., is prepared from ethyl-4-[4-[2-(4-methylphenyl)ethyl]-1-piperazinyl]-benzo[b]thiophene-2-carboxylate (1.30 g, 3.18 mmol, prepared in example 26), dry ammonium chloride ( 0.51 g, 9.6 mmol) and trimethyl aluminum (4.8 mL of a 2M solution in toluene, 9.6 mmol). The free base of the title compound is isolated by flash chromatography (ethyl acetate:hexane, 40:60 , TLC Rf =0.4); 1H NMR (DMSO-d6) δ11.48 (1H, bs), 8.51 (1H, s), 7.82 (1H, d, J=8.2 Hz), 7.56 (1H, t, J=7.9 Hz), 7.19 (4H, m), 7.10 (1H, d, J=7.6 Hz), 3.65 (4H, m), 3.45 (6 H, m), 3.11 (2H, m), 2.29 (3H, s),; 13C NMR (DMSO-d6) δ148.03, 142.47, 135.82, 134.78, 133.93, 131.41, 129.17, 128.52, 117.51, 114.72, 113.96, 107.09, 56.20, 51.03, 48.47, 28.83, 20.59; IR (KBr) 2539, 2448, 1564, 1458, 959 cm-1 ; CI/MS (CH4) 362(100%).

Provenance & Evidence