[OH:1][CH2:2][CH:3]([CH2:18][OH:19])[CH:4]1[C:13]2[C:8](=[CH:9][C:10]([O:16][CH3:17])=[C:11]([O:14][CH3:15])[CH:12]=2)[CH2:7][CH2:6][NH:5]1.[CH2:20]=O.[OH-].[Na+]>>[OH:1][CH2:2][CH:3]1[CH:4]2[C:13]3[C:8]([CH2:7][CH2:6][N:5]2[CH2:20][O:19][CH2:18]1)=[CH:9][C:10]([O:16][CH3:17])=[C:11]([O:14][CH3:15])[CH:12]=36 mmoles (1.6 g) of 1-[bis(hydroxymethyl)-methyl]-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline are stirred with 10 ml of aqueous (30-35%) formaldehyde for half an hour. The reaction mixture is alkalized with 10 ml of a 30% aqueous sodium hydroxide solution and extracted with ethyl acetate. Drying and evaporation of the extract yields the aimed compound in a yield of 89%.
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