[Cl-:1].[Cl:2][CH2:3][CH2:4][NH+:5]([CH2:15][CH2:16]Cl)[CH2:6][CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[F:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[CH2:25][CH2:26][NH2:27].C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>CN(C)C=O.C(OCC)(=O)C.O>[ClH:2].[ClH:1].[F:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[CH2:25][CH2:26][N:27]1[CH2:16][CH2:15][N:5]([CH2:6][CH2:7][CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:4][CH2:3]1To a solution of bis(2-chloroethyl)-(3-phenylpropyl)ammonium chloride (0.593 g, 2 mmol) and 2-(2-fluorophenyl)ethanamine (0.278 g, 2 mmol) in dimethylformamide (6 mL) is added anhydrous potassium carbonate (0.829 g, 6 mmol) and sodium iodide (0.599 g, 4 mmol) successively. The reaction mixture is then stirred at 80° C. for 4.5 hours and then cooled to ambient temperature. Water and ethyl acetate are then added to the resultant reaction mixture. The organic layer is separated, washed 3 times with water and once with brine, dried over anhydrous magnesium sulfate, and concentrated. The residue is dissolved in ethanol. To this solution is added 6 N hydrochloric acid drop wise with cooling until pH 3. The resulting solution is maintained at 4° C. overnight. The resultant crystals are collected by filtration and washed with ethanol and ether to give 108 mg of the title compound (17%).
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