[CH2:1]=O.[CH3:3][NH:4][CH3:5].[CH3:6][C:7]1[O:11][N:10]=[C:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:8]=1[C:18]1[NH:19][C:20]2[C:25]([CH:26]=1)=[CH:24][CH:23]=[CH:22][CH:21]=2.[OH-].[K+]>O1CCOCC1.C(O)(=O)C>[CH3:6][C:7]1[O:11][N:10]=[C:9]([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:8]=1[C:18]1[NH:19][C:20]2[C:25]([C:26]=1[CH2:3][N:4]([CH3:1])[CH3:5])=[CH:24][CH:23]=[CH:22][CH:21]=2A mixture of 20.6 ml. (0.24 mole) 37% aqueous formaldehyde, 18 ml. (0.12 mole) 40% aqueous dimethylamine and 80 ml. acetic acid is cooled to 0° and treated by dropwise addition with 25.5 g. (0.113 mole) 2-(5-methyl-3-phenyl-4-isoxazolyl)-indole in a solution of 45 ml. acetic acid and 125 ml. dioxane. After addition is complete the mixture is stirred for 1 hour at room temperature and poured onto 500 ml. ice-water. The resulting solution is made basic with 20% potassium hydroxide and then extracted with methylene chloride. The methylene chloride is washed with water, brine, dried over anhydrous magnesium sulfate, filtered and evaporated to give 2-(5-methyl-3-phenyl-4-isoxazolyl)-3-(dimethylaminomethyl)-indole.
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