4-Chloroaniline → 4-chloro-N-(2-(diethylamino)ethyl)aniline

HRID 388303

Reaktionsgleichung

Reaktionsgleichung von HRID 388303
[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.Br.Br[CH2:11][CH2:12][N:13]([CH2:16][CH3:17])[CH2:14][CH3:15].C(N(CC)C(C)C)(C)C>C1(C)C=CC=CC=1.CCOC(C)=O.C([O-])(O)=O.[Na+]>[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([NH:6][CH2:11][CH2:12][N:13]([CH2:16][CH3:17])[CH2:14][CH3:15])=[CH:4][CH:3]=1

Komponenten

7

Edukt 3

HCID 78124-ChloroanilineHCID 706072-Bromoethyldiethylammonium bromideHCID 81531Diisopropylethylamine

Produkt 1

HCID 2245014-chloro-N-(2-(diethylamino)ethyl)aniline

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 1140TolueneLösungsmittelHCID 8857Ethyl AcetateLösungsmittelHCID 516892Sodium BicarbonateLösungsmittel

Versuchsvorschrift

4-Chloro-aniline (0.5 g, 3.9 mmol) was added to a solution of 2-bromo-N,N-diethylethylamine hydrobromide (1.12 g, 4.3 mmol) and N,N-diisopropylethylamine (2 mL, 11.7 mmol) in toluene (7.8 mL). The mixture was stirred at room temperature for 5 hours. The mixture was then diluted with EtOAc (30 mL) and saturated NaHCO3 (20 mL). The organic layer was washed with H2O (1×20 mL), dried (Na2SO4), filtered and concentrated to give 4-chloro-N-(2-(diethylamino)ethyl)benzenamine as an oil which was used without purification. MS (APCI+) [M+H]+227.3.

Aufarbeitung

  1. washThe organic layer was washed with H2O (1×20 mL)
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-d117bad35120424baf131ec1e45d11f4
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08377937B2

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