Dimethylamine → N,N-dimethyl-2-(4-nitrophenoxy)ethanamine

HRID 24937Notes

Reaction equation

HRID 24937 reaction equation
Br[CH2:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][CH:6]=1.[CH3:14][NH:15][CH3:16]>CN(C)C=O>[CH3:14][N:15]([CH3:16])[CH2:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][CH:6]=1

Participants

4

Reactant 2

HCID 674DimethylamineHCID 2359871-(2-Bromoethoxy)-4-nitrobenzene

Product 1

HCID 887421N,N-dimethyl-2-(4-nitrophenoxy)ethanamine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4.9 g (20 mmol) of 4-(2-bromoethyloxy)-nitrobenzene and 2.7 g (60 mmol) of dimethylamine in 50 ml of dimethylformamide are heated to 100° C. for 24 hours in a bomb tube. After removal of the solvent in vacuo the residue is taken up in water and extracted with dichloromethane. The organic phase is dried and concentrated by evaporation.

Workup

  1. customAfter removal of the solvent in vacuo the residue
  2. extractionextracted with dichloromethane
  3. customThe organic phase is dried
  4. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-a8e4bf5abd1e4934998ac18b605dab70
Source dataset
uspto-grants-2005_02
Patent number
US06855710B2

Reaction notes

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