反应详情

温度

80 °C

A mixture of compound of Description 5 [5-methoxy-3-(1,2,5,6-tetrahydro-pyridin-3-ylmethyl)-1H-indole] (1.5 g; 0.0062 mol), potassium carbonate (4.3 g; 0.031 mol), KI (0.06 g; 0.0004 mol) and 2-(3-chloropropyl)-2-(4-fluorophenyl)-1,3-dioxolane (1.3 ml; 0.0064 mol) in dry dimethylformamide (30 ml) was heated at 80° C. for 6 hours. The reaction mixture was cool down to room temperature, quenched with water and then extracted with diethyl ether. The organic extract was dried (MgSO4) and evaporated under vacuum. The residue was taken up in a solution of hydrochloric acid (37%; 6 ml) in methanol (30 ml). The resulting mixture was stirred for 2 hours at room temperature. The reaction was then quenched with a saturated solution of aqueous sodium carbonate and the solvent (methanol) was evaporated under vacuum. The residual alkaline aqueous solution was extracted with methylene chloride. The organic extract was dried (MgSO4) and evaporated under vacuum. After purification by Flash Chromatography on silica gel using as eluent methylene chloride/methanol/ammonia (95/5/0,5), the desired compound was obtained (1,72 g). A solution of the compound in ethanol was saturated with gaseous hydrogen chloride. A white solid was precipitated. The title compound hydrochloride was collected by filtration, washed with ethanol and dried under vacuum.

1. temperatureThe reaction mixture was cool down to room temperature
2. customquenched with water
3. extractionextracted with diethyl ether
4. extractionThe organic extract
5. dry with materialwas dried (MgSO4)
6. customevaporated under vacuum
7. customThe reaction was then quenched with a saturated solution of aqueous sodium carbonate
8. customthe solvent (methanol) was evaporated under vacuum
9. extractionThe residual alkaline aqueous solution was extracted with methylene chloride
10. extractionThe organic extract
11. dry with materialwas dried (MgSO4)
12. customevaporated under vacuum
13. customAfter purification by Flash Chromatography on silica gel using as eluent methylene chloride/methanol/ammonia (95/5/0,5)