Cl.[Br:2][C:3]1[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][C:4]=1[CH2:5][CH:6]1[CH2:11][CH2:10][NH:9][CH2:8][CH2:7]1.[OH-].[Na+].[CH2:20](Br)[CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>C(#N)C>[CH2:20]([N:9]1[CH2:8][CH2:7][CH:6]([CH2:5][C:4]2[CH:12]=[C:13]([O:16][CH3:17])[CH:14]=[CH:15][C:3]=2[Br:2])[CH2:11][CH2:10]1)[CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=14-(2-Bromo-5-methoxybenzyl)piperidine hydrochloride (192 mg, 0.60 mmol) was neutralized with a 1N-aqueous sodium hydroxide solution, followed by extraction with diethyl ether, whereby a corresponding free compound was obtained. A mixture of the free compound, phenethyl bromide (110 mg, 0.594 mmol), potassium carbonate (250 mg, 1.81 mmol), potassium iodide (10.3 mg, 0.062 mmol) and acetonitrile (3.6 mL) was heated under reflux under nitrogen for 8 hours. After the inorganic matters were filtered off, the filtrate was concentrated under reduced pressure and the concentration residue was purified by a flash silica gel column chromatography (hexane/ethyl acetate/triethylamine=5/15/0 to 5/15/1) to obtain N-phenethyl-4-(2-bromo-5-methoxy-benzyl)piperidine (134 mg, 58%) as an oil.
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