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

HRID 1270341Notes

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 acetate (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 acetate (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-b938137617bb47e9a54ebd10652e29fc
Source dataset: uspto-grants-2007_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07202254B2

Reaction notes

Loading…