Sodium Azide → 1-(4-Azido-2-fluoro-phenyl)-piperidin-4-one

Participants

Reaction Conditions

Reaction Steps

Sodium nitrite (9.9 g, 144 mmol) was added to an ice-cooled solution of 1-(4-amino-2-fluoro-phenyl)-piperidin-4-one (15 g, 72 mmol), obtained in Preparation 10, in 6 N HCl (60 ml) and the resulting solution was stirred at 0° C. for 0.5 h. An aqueous solution of sodium azide (9.4 g, 144 mmol) and sodium acetate (118 g, 1.44 mol) was then added. The reaction mixture was extracted with ethyl acetatc (100 ml×2) and the combined extracts were washed with 5% sodium bicarbonate solution followed by brine and dried over sodium sulfate. Removal of volatiles left a crude product, which was purified by silica gel column chromatography (ethyl acetate/pet. ether, 1:1) to obtain the title azide (10 g, 63%).

Provenance & Evidence