[CH:1]1([NH2:4])[CH2:3][CH2:2]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[I:19][C:20]1[CH:25]=[CH:24][C:23]([C:26](=O)[CH3:27])=[CH:22][CH:21]=1.C(=O)([O-])O.[Na+]>C(Cl)(Cl)Cl.C(O)(=O)C>[I:19][C:20]1[CH:25]=[CH:24][C:23]([CH:26]([NH:4][CH:1]2[CH2:3][CH2:2]2)[CH3:27])=[CH:22][CH:21]=1Cyclopropylamine (0.85 g), acetic acid (0.89 g), and sodium triacetoxyborohydride (3.2 g) were added to a chloroform (20 mL) solution of 1-(4-iodophenyl)ethanone (1.2 g), and the mixture was stirred in a nitrogen atmosphere for 24 hours at room temperature. A saturated aqueous solution of sodium hydrogen carbonate was added to the reaction mixture, and then the mixture was extracted with chloroform. Then, the organic layer was washed with brine, and dried over anhydrous magnesium sulfate. Then, the desiccant was filtered out, and the solvent was distilled off under reduced pressure. The resulting residue was purified by OH type silica gel chromatography (hexane/ethyl acetate=80/20) to obtain N-[1-(4-iodophenyl)ethyl]cyclopropylamine (colorless oil) (1.3 g, 95%).
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