Potassium Carbonate → 4-Benzyl-2-hydroxymethyl-1-[3-(5-(1,2,4-triazol-4-yl)-1H-indol-3-yl)propyl]piperazine oxalate

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A mixture of 4-benzyl-2-hydroxymethyl-1-(5,5-dimethoxypentyl)piperazine (245 mg, 0.73 mmol) and 4-(1,2,4-triazol-4-yl)phenylhydrazine (127 mg, 0.73 mmol) in 4% H2SO4 (8 mL) was heated at reflux overnight. The solution was basified using sat. K2CO3 solution and extracted with nBuOH (2×30 mL). The combined organic layers were evaporated and the residue chromatographed on silica gel, eluting with CH2Cl2 :MeOH:NH3 (90:10:1). The title compound (73 mg, 23%) was isolated as a pale yellow foam. The free base was converted to the oxalate salt by treatment with oxalic acid in methanol/water. mp 130°-132° C. Found: C, 59.90; H, 6.18; N, 15.35%. C25 H30N6O. 1.3 (C2H2O4). 0.3 (H2O). 0.1 (Et2O) requires C, 60.01; H, 6.15; N, 15.00%. 1H NMR (360 MHz, d6 -DMSO) δ 1.92-2.10 (2H, m), 2.36-2.46 (2H, m), 2.70-3.06 (6H, m), 3.14-3.36 (3H, m), 3.57-3.72 (4H, m), 7.24-7.40 (7H, m), 7.49 (1H, d, J=8.6 Hz), 7.79 (1H, s), 8.99 (2H, s), 11.19 (1H, br s).

Provenance & Evidence