反应详情

Phosphorus oxychloride (0.35 mL, 3.74 mmol) was added dropwise to cooled dimethylformamide (0.8 mL, 10.3 mmol). After stirring at room temperature for 30 minutes, the mixture was cooled to −5° C. and a solution of [3-(6,6-dimethyl-4,5,6,7-tetrahydro-1H-indol-3-yl)-propyl]-diethyl-amine (0.9 g, 3.4 mmol) in dimethylformamide (2 mL) was added dropwise. The mixture was stirred at room temperature for 3 hours. The reaction was quenched with ice, followed by 10 N potassium to adjust the pH to 10–11. After stirring at room temperature for 1 hour, the reaction was extracted with ethyl acetate and the extract was washed with brine, dried and concentrated to give 0.55 g of 3-(3-diethylamino-propyl)-6,6-dimethyl-4,5,6,7-tetrahydro-1H-indole-2-carbaldehyde. 1H-NMR (360 MHz, dimethylsulfoxide-d6) δ 11.23 (br, s, 1H, NH), 9.41 (s, 1H, CHO), 2.61 (t, 2H, CH2), 2.30–2.43 (m, 10 H, 5×CH2), 1.58 (m, 2H, CH2), 1.45 (t, 2H, CH2), 0.93 (s, 6H, 2×CH3), 0.89 (t, 6H, CH3). MS m/z 290 [M+].

1. temperaturethe mixture was cooled to −5° C.
2. stirringThe mixture was stirred at room temperature for 3 hours
3. customThe reaction was quenched with ice
4. stirringAfter stirring at room temperature for 1 hour
5. extractionthe reaction was extracted with ethyl acetate
6. washthe extract was washed with brine
7. customdried
8. concentrationconcentrated