[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH3:7][O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][C:18]=1[O:19][CH3:20])[CH2:15][N:14]([C:21]([CH:23]1[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]1)=O)[CH2:13][CH2:12]2.O.[OH-].[Na+]>O1CCCC1>[CH3:7][O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][C:18]=1[O:19][CH3:20])[CH2:15][N:14]([CH2:21][CH:23]1[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]1)[CH2:13][CH2:12]2A 1 M solution of LiAlH4 in dry tetrahydrofuran (12 ml) was added dropwise to a solution of (6,7-dimethoxy-3,4-dihydroisoquinolin-2(1H)-yl)(piperidin-4-yl)methanone (2 g, 6.6 mmol) in dry tetrahydrofuran (60 ml) under argon atmosphere. The mixture was refluxed overnight. Water was added to the crude, made alkaline with 1 N NaOH and the salts formed was filtered over celite. Extraction with ethyl acetate yielded a solution that was dried with Na2SO4 and concentrated in vacuo to give and oil that was purified by flash chromatography.
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