CN1CCC(=O)CC1.BrC1C2C(=CC=CC=2)C=CN=1.C([Li])CCC.[ClH:25].[CH3:26][N:27]1[CH2:32][CH2:31][C:30]([C:34]2[C:43]3[C:38](=[CH:39][CH:40]=[CH:41][CH:42]=3)[CH:37]=[CH:36][N:35]=2)([O-:33])[CH2:29][CH2:28]1.[Li+]>O.CCOCC>[ClH:25].[ClH:25].[CH3:26][N:27]1[CH2:28][CH2:29][C:30]([C:34]2[C:43]3[C:38](=[CH:39][CH:40]=[CH:41][CH:42]=3)[CH:37]=[CH:36][N:35]=2)([OH:33])[CH2:31][CH2:32]1A solution of 11.3 g. of 1-methylpiperidin-4-one in 120 ml. of ether is added dropwise to a stirred isoquinolyl-1-lithium solution, freshly prepared from 20.8 g. of 1-bromoisoquinoline and n-butyllithium in 400 ml. of ether, at 0°, under dry nitrogen. The mixture is stirred for 2 hours more at 0°. Water (50 ml.) and then 100 ml. of 5% hydrochloric acid are added dropwise to decompose the lithium 1-methyl-4-(1-isoquinolyl)-piperidin-4-olate formed. The mixture is worked up in the customary manner to give 1-methyl-4-(1-isoquinolyl)-piperidin-4-ol, dihydrochloride, m.p. 265°-266°.
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