[CH2:1]([N:8]([CH2:12][C:13]1[CH:17]=[CH:16][O:15][CH:14]=1)[CH2:9][CH2:10]O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.C1(C)C=CC(S([Cl:34])(=O)=O)=CC=1.O>CN(C)C1C=CN=CC=1.ClCCl>[CH2:1]([N:8]([CH2:9][CH2:10][Cl:34])[CH2:12][C:13]1[CH:17]=[CH:16][O:15][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
To a solution of 0.397 g (1.716 mmol) of 2-[benzyl-(3-furylmethyl)amino]ethanol, 0.36 ml (2.6 mmol) of triethylamine and 10 mg of 4-dimethylaminopyridine in 30 ml of dichloromethane, 0.39 g (2.1 mmol) of p-toluenesulfonyl chloride was added at room temperature, followed by stirring at room temperature for 6 hours. The reaction mixture was poured into water and extracted with dichloromethane 3 times. The combined organic layer was dried over anhydrous magnesium sulfate; the solvent was distilled off under reduced pressure. The resulting crude product was purified by silica gel column chromatography (hexane/ethyl acetate=15/1 to 9/1) to yield N-benzyl-N-(3-furylmethy)-2-chloroethylamine.
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