3-Iodoaniline → HCID 19081605, compound

Participants

Reaction Steps

13bd) A mixture of 2 g of 3-iodoaniline and 1.26 ml of tetrahydro-4H-pyran-4-one is boiled in 50 ml of toluene on a water separator for 4 hrs. The solution of the imine which remains behind is treated with 20 ml of methanol and 520 mg of sodium borohydride are added in portions. The mixture is stirred at room temperature for 16 hrs., then poured into water and extracted with ethyl acetate. Chromatography on silica gel with ethyl acetate/hexane 3:7 gives 559 mg of (3-iodo-phenyl)-(tetrahydropyran-4-yl)-amine as a colourless oil. Yield: 20%. Mass spectrum: peaks inter alia at m/e: 303 (M+, 100%), 245 (40%), 219 (40%), 130 (90%), 117 (62%).

Provenance & Evidence