Dimethylamine → 4-[2-(Dimethylamino)ethoxy]aniline

HRID 639373Notes

Reaction equation

HRID 639373 reaction equation
Cl[CH2:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([NH2:11])=[CH:7][CH:6]=1.[CH3:12][NH:13][CH3:14]>[OH-].[Na+]>[CH3:12][N:13]([CH3:14])[CH2:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([NH2:11])=[CH:7][CH:6]=1

Participants

4

Reactant 2

HCID 674DimethylamineHCID 1196994-(2-Chloroethoxy)aniline

Product 1

HCID 64846554-[2-(Dimethylamino)ethoxy]aniline

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

11.15 g (0.065 Mol) of 4-(2-Chloro-ethoxy)-phenylamine is suspended in 150 mL (1.18 Mol) of dimethylamine (40% in water; Fluka 38940) and heated under stirring in a steel pressure reactor at 4 bar for 21 h. After cooling the reaction mixture is diluted with 150 mL of 2N NaOH and extracted with ethyl acetate. The combined organic layers are washed with water, dried (Na2SO4), filtered and evaporated under reduced pressure to obtain 4-(2-dimethylamino-ethoxy)-phenylamine. Title compound: ES-MS: 181 [M+H]+; single peak at tR=1.10 min (System 1).

Workup

  1. temperatureheated
  2. temperatureAfter cooling the reaction mixture
  3. extractionextracted with ethyl acetate
  4. washThe combined organic layers are washed with water
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-46ac115a262b4efd8020de82c5e98e43
Source dataset
uspto-grants-2010_04
Patent number
US07691855B2

Reaction notes

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