[CH2:1]([C:3]1[C:7]([C:8]2[NH:9][C:10]3[C:15]([C:16]=2[C:17](=[O:19])[CH3:18])=[CH:14][CH:13]=[CH:12][CH:11]=3)=[C:6]([CH3:20])[O:5][N:4]=1)[CH3:2].Cl.[CH3:22][NH:23][CH3:24].Cl.[CH2:26]=O>C(O)C>[CH3:22][N:23]([CH3:26])[CH2:24][CH2:18][C:17]([C:16]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[NH:9][C:8]=1[C:7]1[C:3]([CH2:1][CH3:2])=[N:4][O:5][C:6]=1[CH3:20])=[O:19]A mixture of 12 g. (0.045 mole) of 2-(3-ethyl-5-methyl-4-isoxazolyl)-3-acetyl indole, 4 g. (0.049 mole) of dimethylamine hydrochloride, and 0.5 ml. concentrated hydrochloric acid in 70 ml. of ethanol is heated to reflux and treated by the portionwise addition of 14 g. (0.470 mole) of paraformaldehyde over 5 hours. The resulting mixture is refluxed an additional 24 hours, cooled and evaporated in vacuo. The residue is then dissolved in 300 ml. methylene chloride and washed with 200 ml. 2 N hydrochloric acid, the aqueous acid is cooled and made basic with 2 N sodium hydroxide and extracted with methylene chloride. The organic layer is dried over anhydrous magnesium sulfate, filtered and evaporated in vacuo. The residue is crystallized from ether to give 3-dimethylamino-1-[2-(3-ethyl-5-methyl-4-isoxazolyl)-1H-indol-3-yl]-1-propanone, m.p. 146°-148° C.
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