Morpholine → 4-(4-Methoxy-3-nitrophenyl)morpholine

HRID 2250795Notes

Reaction equation

HRID 2250795 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[C:4]([N+:10]([O-:12])=[O:11])[CH:3]=1.[NH:13]1[CH2:18][CH2:17][O:16][CH2:15][CH2:14]1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>C(COC)OC.C(OCC)(=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:9][O:8][C:5]1[CH:6]=[CH:7][C:2]([N:13]2[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)=[CH:3][C:4]=1[N+:10]([O-:12])=[O:11]

Participants

7

Reactant 3

HCID 8083MorpholineHCID 62657Potassium Phosphate, TribasicHCID 1185334-Bromo-2-nitroanisole

Product 1

HCID 177470104-(4-Methoxy-3-nitrophenyl)morpholineYield 70%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 80711,2-DimethoxyethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

4-Bromo-2-nitroanisol (8.5 g, 36 mmol), morpholine (3.8 ml, 44 mmol), potassium phosphate (11 g, 51 mmol), 2-biphenyl-dicyclohexyl phosphine (960 mg, 2.7 mmol) and palladium(II)acetate (411 mg, 1.8 mmol) are dissolved in dimethoxyethane (80 ml) and stirred at 80° C. for 96 hours. The mixture is then cooled to room temperature, diluted with ethyl acetate (50 ml) and filtrated through dicalite. Flash chromatography on silica (eluent dichloromethane/methanol 99: 1) affords the product as red solid (6.0 g, 69%). MS: m/e=238 (M+).

Workup

  1. temperatureThe mixture is then cooled to room temperature
  2. filtrationfiltrated through dicalite

Sources & evidence

ORD record
ord-b9b2fb2f46ab441e866f8049c56d35f8
Source dataset
uspto-grants-2008_01
Patent number
US07317007B2

Reaction notes

Loading…