4-Aminophenol → 4-(3-(tetrahydro-2H-pyran-4-yl)pyridin-2-yloxy)aniline

HRID 473641Notes

Reaction equation

HRID 473641 reaction equation
F[C:2]1[C:7]([CH:8]2[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)=[CH:6][CH:5]=[CH:4][N:3]=1.[NH2:14][C:15]1[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[Cl-].[Na+]>CS(C)=O.O>[O:11]1[CH2:12][CH2:13][CH:8]([C:7]2[C:2]([O:21][C:18]3[CH:19]=[CH:20][C:15]([NH2:14])=[CH:16][CH:17]=3)=[N:3][CH:4]=[CH:5][CH:6]=2)[CH2:9][CH2:10]1

Participants

7

Reactant 4

HCID 4034-AminophenolHCID 5234Sodium ChlorideHCID 10796Cesium carbonateHCID 593271552-Fluoro-3-(tetrahydro-2H-pyran-4-yl)pyridine

Product 1

HCID 593271274-(3-(tetrahydro-2H-pyran-4-yl)pyridin-2-yloxy)aniline

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

To a rbf was added 2-fluoro-3-(tetrahydro-2H-pyran-4-yl)pyridine (2.156 g, 11.90 mmol), 4-aminophenol (1.948 g, 17.85 mmol), and cesium carbonate (11.63 g, 35.7 mmol) in DMSO (39.7 mL) at 110° C. to stir overnight. Upon completion, the reaction mixture was diluted with water and sat sodium chloride solution and extracted with dichloromethane. The organic extract was washed with water and sat sodium chloride solution, dried with magnesium sulfate, filtered, and concentrated. MS (ESI, pos. ion) m/z: 271.1.

Workup

  1. extractionextracted with dichloromethane
  2. extractionThe organic extract
  3. washwas washed with water
  4. dry with materialdried with magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-c39a5bf74ecb4f9783f2f7f937155318
Source dataset
uspto-grants-2014_01
Patent number
US08637500B2

Reaction notes

Loading…