Sodium Iodide → HCID 15168576, compound

Participants

Reaction Steps

To a solution of trans-4-amino-5,7-dichloro-2-methoxycarbonyl-1,2,3,4-tetrahydroquinoline hydrochloride (0.300 g, 0.96 mmol) in anhydrous DMF (10 ml) was added triethylamine (0.403 ml, 2.89 mmol), benzyl bromide (0.230 ml, 1.92 mmol) and a catalytic quantity of sodium iodide. This mixture was stirred under an atmosphere of nitrogen at room temperature for 90 hours. The solvent was removed in vacuo and the residue obtained was partitioned between distilled water (100 ml) and ethyl acetate (200 ml). The organic layer was washed with saturated sodium hydrogen carbonate (2×100 ml), brine (2×100 ml) and distilled water (2×100 ml), dried (MgSO4) and concentrated in vacuo. The residue was purified by chromatrography on silica gel (using from 10% ethyl acetate in hexane to 50% ethyl acetate in hexane as eluents) to give the title compound as colourless crystals, m.p. 112°-114° C. δ (360 MHz, DMSO), 1.41 (1H, ddd, J=13.4, 12.3 and 3.1 Hz, CHACHBHCCHD), 2.33 (1H, dm, J=13.4 Hz, CHACHBHCCHD), 3.73 (3H, s, CO2CH3), 3.84 (2H, 2 d, J=13.5 Hz, CH2C6H ), 4.13 (1H, m, CHACHBHCCHD), 4.27 (1H, dd, J=12.3 and 2.8 Hz, CHACHBHCCHD), 6.60 (1H, d, J=2.1 Hz, 6-H or 8-H), 6.73 (1H, s, ArNH, 6.78 (1H, d, J=7.69 (1H, d, 2.1 Hz, 6-H or 8-H), 7.28 (3H, m, ArH), 7.37 (2H, m, ArH), 7.69 (1H, m, CHNHCH2); m/e (CI+) 365 (M+1).

Provenance & Evidence