[C:1](O)(=O)C.[CH3:5][NH:6][CH3:7].C=O.[CH3:10][O:11][C:12]1[C:13]([CH3:21])=[C:14]2[C:18](=[CH:19][CH:20]=1)[NH:17][CH:16]=[CH:15]2>C(O)C>[CH3:10][O:11][C:12]1[C:13]([CH3:21])=[C:14]2[C:7](=[CH:19][CH:20]=1)[NH:6][CH:5]=[C:15]2[CH2:16][N:17]([CH3:1])[CH3:18]Acetic acid (0.39 mL) and dimethylamine (0.85 mL of a 40% aqueous solution) were added to a suspension of paraformaldehyde (0.21 g) in 25 mL ethanol. The mixture was heated to reflux until it was clear. The solution was cooled to rt and a solution of 5-methoxy-4-methyl-indole (1.0 g) in 25 mL of ethanol was added. The reaction was heated to reflux for 3 h. The volatiles were removed in vacuo to yield (5-methoxy-4-methyl-1H-indol-3-ylmethyl)-dimethylamine (1.0 g).
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