[OH-].[Na+].[S:3]1[CH:7]=[CH:6][C:5]2[CH:8]=[C:9]([CH2:12][CH2:13][OH:14])[CH:10]=[CH:11][C:4]1=2.Cl.Cl[CH2:17][CH2:18][N:19]([CH2:22][CH3:23])[CH2:20][CH3:21]>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1.O>[S:3]1[CH:7]=[CH:6][C:5]2[CH:8]=[C:9]([CH2:12][CH2:13][O:14][CH2:17][CH2:18][N:19]([CH2:22][CH3:23])[CH2:20][CH3:21])[CH:10]=[CH:11][C:4]1=2In a mixture of 10 mL of 50% (W/V) aqueous solution of sodium hydroxide and 2 mL of toluene is suspended 2.00 g of 2-benzo[b]thiophen-5-yl-1-ethanol. To the suspension are added 2.51 g of N-(2-chloroethyl)-N,N-diethylamine hydrochloride and 0.38 g of tetra-n-butylammonium hydrogen sulfate, and the resulting mixture is heated under reflux for one hour. Water and toluene are added to the reaction mixture, and the organic layer is separated. The organic layer is washed successively with water and saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate, the solvent is distilled off under reduced pressure, and the residue is purified by column chromatography (eluent:chloroform:methanol=10:1) to obtain 3.10 g of N-[2-(2-benzo[b]thiophen-5-ylethoxy)ethyl]-N,N-diethylamine as an oily product.
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