Pyridine → HCID 19022613, compound

Participants

Reaction Steps

A solution of 1.0 g (3.08 mmol) of 2,3,4,5-tetrahydro-3-(methoxycarbonyl)-4-(4-methoxyphenyl)-1H-1-benzazepin-2-one [prepared by the method of Floyd, et al., J. Med. Chem., 35, 756-772 (1992)]in 10 mL of pyridine was treated with 1.65g (12.3 mmol, 4eq) of lithium iodide and the resulting mixture refluxed in an oil bath under a nitrogen atmosphere for 20 hours. The dark brown mixture was cooled to room temperature and diluted with ethyl acetate. The organic layer was washed with 1N HCl (3×50 mL) and water, dried over anhydrous magnesium sulfate and filtered. Evaporation of the solvent followed by column chromatography on silica gel gave 520mg (63%) of the product. 1H NMR (200 MHz, CDCl3): 257 (dd; 4,8 Hz; 2H), 2.81 (dd; 7, 13 Hz; 1H), 3.13 (dd; 8, 14 Hz; 1H), 3.63 (dt; 14, 7 Hz; 1H), 3.74 (s, 3H), 6.82 (d, 8 Hz, 2H), 7.02 (d, 8 Hz, 1H), 7.14-7.34 (m, 5H), 8.03 (br s, 1H). FAB-MS: calculated for C17H17NO2 267; found 267 (100%).

Provenance & Evidence