Sodium Azide → HCID 21069827, compound

HRID 1788123Notes

Reaction equation

HRID 1788123 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([F:9])=[CH:5][C:4]=1[C:10]([N:12]1[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1)=[O:11].[N-:18]=[N+:19]=[N-:20].[Na+]>CN(C)C=O>[N:18]([CH2:2][C:3]1[CH:8]=[CH:7][C:6]([F:9])=[CH:5][C:4]=1[C:10]([N:12]1[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1)=[O:11])=[N+:19]=[N-:20]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 21069832HCID 21069832, compound

Product 1

HCID 21069827HCID 21069827, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of intermediate 42, (2-(bromomethyl)-5-fluorophenyl)(morpholino)methanone, (1.0 g, 3.32 mmol) in dimethylformamide (10 mL) was added sodium azide (230 mg, 3.5 mmol) and the mixture stirred under a nitrogen atmosphere for 1 h. The solvent was evaporated in vacuo, and the residue dissolved in CH2Cl2, then washed with water. The organic phase was dried (Na2SO4), filtered, concentrated, and the residue purified by column chromatography (SiO2, CH2Cl2) to provide 770 mg (Yield 88%) of the title compound as an oil: 1H NMR (300 MHz, CDCl3) δ ppm: 3.27 (2H, s) 3.51-3.65 (2H, m) 3.66-3.97 (4H, m) 4.38 (2H, brs) 6.92 (1H, dd, J=8.2, 2.7 Hz) 7.07 (1H, dt, J=8.5, 3 Hz) 7.34 (1 H, dd, J=8.4, 5.5 Hz); LC/MS m/z 265 (M+H).

Workup

  1. customThe solvent was evaporated in vacuo
  2. dissolutionthe residue dissolved in CH2Cl2
  3. washwashed with water
  4. dry with materialThe organic phase was dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customthe residue purified by column chromatography (SiO2, CH2Cl2)

Sources & evidence

ORD record
ord-f9c750b9df7c47f889d1206627e75429
Source dataset
uspto-grants-2009_03
Patent number
US07511037B2

Reaction notes

Loading…