Aluminum(III) Chloride → 1-{3-[4-(2,3-Dichlorophenyl)piperazin-1-yl]propyl}-2,3-dihydro-1H-indole, Hydrochloride

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Reaction Conditions

Reaction Steps

Lithium aluminium hydride (1.8 g) was suspended in tetrahydrofuran (30 mL) at 0° C., and the suspension was added a solution of aluminium trichloride (1.8 g) in tetrahydrofuran (30 mL) at 0–5° C. over 15 min. To this mixture, a solution of 1a, 3-[4-(2,3-dichlorophenyl)piperazin-1-yl]-1-(2,3-dihydro-1H-indol-1-yl)propan-1-one (5 g) in tetrahydrofuran (50 mL) was added at a temperature of 0–10° C. The resulting mixture was stirred for 30 min at 5° C. and then for 2 h at room temperature. The reaction mixture was quenched with water and sodium hydroxide (28%) and filtered. The organic phase was evaporated to dryness in vacuo, and the title compound was precipitated as the hydrochloride salt and recrystallised from ethanol (3.8 g). Mp 214–226° C. 1H NMR (DMSO-d6): 2.05–2.20 (m, 2H); 2.95 (t, 2H); 3.10–3.35 (m, 8H); 3.35–3.50 (m, 4H); 3.60 (d, 2H); 6.70 (b s, 2H); 7.05 (t, 1H); 7.10 (d, 1H); 7.20 (d, 1H); 7.30–7.40 (m, 2H); 11.45 (b s). MS m/z: 390 (MH+), 271, 132.

Provenance & Evidence