[CH3:1][I:2].[N:3]1([CH2:10][CH2:11][CH:12]([C:19]2[CH:24]=[C:23]([CH3:25])[CH:22]=[CH:21][C:20]=2[OH:26])[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1>C(Cl)Cl>[I-:2].[OH:26][C:20]1[CH:21]=[CH:22][C:23]([CH3:25])=[CH:24][C:19]=1[CH:12]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH2:11][CH2:10][N+:3]1([CH3:1])[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1Methyl iodide (10 equivalents) was added to a solution of the free base 2-(3-azepan-1-yl-1-phenylpropyl)-4-methylphenol of Example 30 (0.3 g, 1.02 mmol) in CH2Cl2 (2 mL). The reaction mixture was stirred overnight at room temperature. The solution was concentrated to initiate precipitation of the resulting quaternary ammonium salt. The white precipitate was filtered out, washed with diethyl ether and dried under vacuum to give a quaternized salt.
Loading…