Dimethylformamide → 3-Azido-6-fluoro-1,3,4,5-tetrahydro-2H-1-benzazepin-2-one

Participants

Reaction Steps

DMF (300 ml) was added to a mixture of 6-fluoro-3-iodo-1,3,4,5-tetrahydro-1-benzazepin-2-one (42.5 g) and sodium azide (13.59 g, 209 mmol) at room temperature and the reaction was stirred overnight. The mixture was diluted with water (2000 mL) and a precipitate formed, which was filtered off and washed with water. The precipitate was taken up in dichloromethane and washed with brine, dried over Na2SO4, filtered, and concentrated. The crude 3-Azido-6-fluoro-1,3,4,5-tetrahydro-1-benzazepin-2-one was isolated as a dark brown solid. Residual DMF remains in the sample, which was used without further manipulation in the next reaction.

Provenance & Evidence