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Phosphorus oxychloride (0.5 mL, 5.1 mmol) was added dropwise to ice-cooled dimethylformamide (1.1 mL, 14.1 mmol) and then stirred at room temperature for 30 minutes. A solution of [3-(6,6-dimethyl-4,5,6,7-tetrahydro-1H-indol-3-yl)-propyl]-dimethyl-amine (1.1 g, 4.6 mmol) in dimethylformamide (2 mL) was added dropwise at −5° C. The mixture was stirred at room temperature overnight. Ice cubes were added to the reaction mixture followed by the addition of 10 N potassium hydroxide to pH 11–12 and stirring for one hour. The mixture was extracted with ethyl acetate and the extract washed with brine and concentrated. The residue was chromatographed (5%-10% methanol in dichloromethane) to give 650 mg of 3-(3-dimethylamino-propyl)-6,6-dimethyl-4,5,6,7-tetrahydro-1H-indole-2-carbaldehyde as a brown solid. 1H-NMR (360 MHz, dimethylsulfoxide-d6) δ 11.25 (br s, 1H, NH), 9.41 (s, 1H, CHO), 2.62 (t, 2H, CH2), 2.36 (t, 2H, CH2), 2.30 (s, 2H, CH2), 2.21 (t, 2H, CH2), 2.12 (s, 6H, 2×CH3), 1.60 (m, 2H, CH2), 1.46 (t, 2H, CH2), 0.93 (s, 6H, 2×CH3). MS m/z 262 [M+].

1. stirringThe mixture was stirred at room temperature overnight
2. additionIce cubes were added to the reaction mixture
3. stirringstirring for one hour
4. extractionThe mixture was extracted with ethyl acetate
5. washthe extract washed with brine
6. concentrationconcentrated
7. customThe residue was chromatographed (5%-10% methanol in dichloromethane)