Water → 4-(4-Nitrophenyl)morpholine

HRID 885921Notes

Reaction equation

HRID 885921 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=1.[NH:11]1[CH2:16][CH2:15][O:14][CH2:13][CH2:12]1.C(=O)([O-])[O-].[Cs+].[Cs+].O>CN(C=O)C>[N+:8]([C:5]1[CH:6]=[CH:7][C:2]([N:11]2[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)=[CH:3][CH:4]=1)([O-:10])=[O:9]

Participants

6

Reactant 4

HCID 962WaterHCID 8083MorpholineHCID 9590p-FluoronitrobenzeneHCID 10796Cesium carbonate

Product 1

HCID 252224-(4-Nitrophenyl)morpholineYield 88.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a stirred solution of 4-fluoronitrobenzene (5.0 g, 35.43 mmol) in DMF (40 mL) were added morpholine (4.7 mL, 53.15 mmol) and cesium carbonate (17.3 g, 53.15 mmol). The reaction mixture was stirred at 60° C. for 48 h, then water (50 mL) was added. The solid formed was filtered and washed with water (5×100 mL), then Et2O (3×50 mL) to give the title compound (6.5 g, 88%) as a yellow solid that was used without further purification. δH (DMSO-d6) 8.12-8.02 (2H, m), 7.09-7.00 (2H, m), 3.79-3.68 (4H, m), 4.46-3.37 (4H, m). LCMS (ES+) 208.9 (M+H)+, RT 2.49 minutes (Method 3).

Workup

  1. customThe solid formed
  2. filtrationwas filtered
  3. washwashed with water (5×100 mL)

Sources & evidence

ORD record
ord-ce72f90219034ba5ab60148c706b0431
Source dataset
uspto-grants-2012_08
Patent number
US08242116B2

Reaction notes

Loading…