[OH:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[CH:5]2.Cl.Cl[CH2:13][CH2:14][N:15]1[CH2:20][CH2:19][O:18][CH2:17][CH2:16]1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[NH:7]1[C:8]2[C:4](=[CH:3][C:2]([O:1][CH2:13][CH2:14][N:15]3[CH2:20][CH2:19][O:18][CH2:17][CH2:16]3)=[CH:10][CH:9]=2)[CH:5]=[CH:6]1A solution of 5-hydroxy-1H-indole (0.13 g, 1.0 mmol) in acetonitrile (10 mL) was successively added with N-(2-chloroethyl)morpholine hydrochloride (0.19 g, 1.0 mmol), and potassium carbonate (0.28 g, 2.0 mmol), and the mixture was stirred at room temperature for 72 hours. The solvent was evaporated under reduced pressure, then the residue was added with ethyl acetate, and the organic layer was washed successively with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and then the residue was subjected to silica gel column chromatography (eluted with hexane/ethyl acetate (50:50→20:80)) to obtain 4-[2-(1H-indol-5-yloxy)ethyl]morpholine (0.12 g, 50%).
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