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

HRID 895128Notes

Reaction equation

N([O-])=O.[Na+].[NH2:5][C:6]1[CH:11]=[CH:10][C:9]([N:12]2[CH2:17][CH2:16][C:15](=[O:18])[CH2:14][CH2:13]2)=[C:8]([F:19])[CH:7]=1.[N-:20]=[N+:21]=[N-].[Na+].C([O-])(=O)C.[Na+]>Cl>[N:5]([C:6]1[CH:11]=[CH:10][C:9]([N:12]2[CH2:17][CH2:16][C:15](=[O:18])[CH2:14][CH2:13]2)=[C:8]([F:19])[CH:7]=1)=[N+:20]=[N-:21]

Participants

Conditions

Temperature: 0 °C

Procedure

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%).

Workup

extractionThe reaction mixture was extracted with ethyl acetatc (100 ml×2)
washthe combined extracts were washed with 5% sodium bicarbonate solution
dry with materialdried over sodium sulfate
customRemoval of volatiles
waitleft a crude product, which
customwas purified by silica gel column chromatography (ethyl acetate/pet. ether, 1:1)

Sources & evidence

ORD record: ord-4be3a8fe137b4e1b8d483b1703a2602e
Source dataset: uspto-grants-2005_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06914058B2

Reaction notes

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