Water → Diethyl[2-(4-nitrophenoxy)ethyl]amine

HRID 1792763Notes

Reaction equation

HRID 1792763 reaction equation
O.[N+:2]([C:5]1[CH:11]=[CH:10][C:8]([O-:9])=[CH:7][CH:6]=1)([O-:4])=[O:3].[Na+].Cl.[CH2:14]([N:16]([CH2:20][CH3:21])[CH2:17][CH2:18]Cl)[CH3:15].C(=O)([O-])[O-].[K+].[K+]>C1(C)C(C)=CC=CC=1>[CH2:14]([N:16]([CH2:20][CH3:21])[CH2:17][CH2:18][O:9][C:8]1[CH:10]=[CH:11][C:5]([N+:2]([O-:4])=[O:3])=[CH:6][CH:7]=1)[CH3:15]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 13214p-nitrophenol sodium saltHCID 133631-Chloro-2-(diethylamine)ethane hydrochloride

Product 1

HCID 88294Diethyl[2-(4-nitrophenoxy)ethyl]amineYield 67.1%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

Water (8 ml) and xylene (35 ml) were added to a mixture of sodium 4-nitrophenoxide (10.5 g, 65 mmol), 2-(diethylamino)ethylchloride hydrochloride (8.6 g, 50 mmol) and potassium carbonate (10.4 g, 75 mmol) and the resulting mixture was heated at reflux for 2 hours. A Dean-Stark apparatus was then fitted and the water was removed. The organic solution was allowed to cool to ambient temperature and left to stand for 18 hours. The solution was decanted from the precipitated solid and the volatiles were removed from the decanted solution by evaporation to give the title compound (8.0 g, 52% yield) as an oil. NMR: 0.90 (t, 6H), 2.50 (q, 2H), 2.89 (t, 2H), 4.15 (t, 2H), 7.15 (d, 2H), 8.18 (d, 2H); m/z: 239 [MH]+.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureat reflux for 2 hours
  3. customA Dean-Stark apparatus was then fitted
  4. customthe water was removed
  5. waitleft
  6. customThe solution was decanted from the precipitated solid
  7. customthe volatiles were removed from the decanted solution by evaporation

Sources & evidence

ORD record
ord-40c029c48eb649dba92432924394188f
Source dataset
uspto-grants-2006_07
Patent number
US07078410B2

Reaction notes

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