Potassium Carbonate → 3-{3-[4-(2,3-Dichlorophenyl)piperazin-1-yl]propyl}-1H-indole, hydrochloride

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Reaction Steps

A mixture of 3-(3-bromopropyl)-1H-indole (1.19 g), potassium carbonate (1.4 g) and 1-(2,3-dichlorophenyl)piperazine (1.27 g) in anhydrous acetonitrile (10 mL) was boiled under reflux for 5 h and cooled to room temperature. The mixture was added silicagel (7 g), and the solvent was evaporated in vacuo. The compound was purified by flash chromatography on silicagel (eluent: ethylacetate/heptane/triethylamine 49:49:2). Fractions containing the compound were combined and evaporated in vacuo. Recrystallisation from acetonitrile gave the title compound as a white crystalline material. The compound was precipitated as the hydrochloride salt (1 g). Mp 241–242° C. 1H NMR (DMSO-d6): 2.10–2.25 (m, 2H); 2.75 (t, 2H); 3.10–3.30 (m, 6H); 3.40 (t, 2H); 3.60 (d, 2H); 7.00 (t, 1H); 7.05 (t, 1H); 7.15 (d, 1H); 7.25 (s, 1H); 7.30–7.40 (m, 3H); 7.55 (d, 1H); 10.90 (b s, 1H); 11.40 (b s, 1H). Ms m/z: 388 (MH+).

Provenance & Evidence