Sodium Azide → HCID 20810160, compound

HRID 1270343Notes

Reaction equation

N([O-])=O.[Na+].[NH2:5][C:6]1[CH:11]=[C:10]([F:12])[C:9]([N:13]2[CH2:18][CH2:17][C:16](=[O:19])[CH2:15][CH2:14]2)=[C:8]([F:20])[CH:7]=1.[N-:21]=[N+:22]=[N-].[Na+].C([O-])(=O)C.[Na+]>Cl>[N:5]([C:6]1[CH:11]=[C:10]([F:12])[C:9]([N:13]2[CH2:14][CH2:15][C:16](=[O:19])[CH2:17][CH2:18]2)=[C:8]([F:20])[CH:7]=1)=[N+:21]=[N-:22]

Participants

Conditions

Temperature: 0 °C

Procedure

Sodium nitrite (2.40 g, 35.30 mmol) was added to an ice cooled solution of 1-(4-amino-2,6-difluorophenyl)-piperidin-4-one (4.00 g, 17.69 mmol), obtained in Preparation 17, in 6 N HCl (10 ml) and the resulting solution was stirred at 0° C. for 0.5 h. The reaction mixture was quenched with an aqueous solution of sodium azide (2.30 g, 35.3 mmol) and sodium acetate (29.0 g, 353 mmol). The reaction mixture was extracted with ethylacetate (100 ml×2) and the combined extract was washed with water followed by brine. The ethylacetate extract was dried over sodium sulfate and concentrated under reduced pressure. The resulting residue was purified by column chromatography (ethylacetate/pet ether; 1:9) to yield the title compound (2.20 g, 55%).

Workup

extractionThe reaction mixture was extracted with ethylacetate (100 ml×2)
extractionthe combined extract
washwas washed with water
extractionThe ethylacetate extract
dry with materialwas dried over sodium sulfate
concentrationconcentrated under reduced pressure
customThe resulting residue was purified by column chromatography (ethylacetate/pet ether; 1:9)

Sources & evidence

ORD record: ord-fa561680b5794fc3bb0a5022a3158ecf
Source dataset: uspto-grants-2007_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07202254B2

Reaction notes

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