3-Nitrophenol → N,N-diethyl-N-[3-(3-nitrophenoxy)propyl]amine

HRID 17658

Reaktionsgleichung

Reaktionsgleichung von HRID 17658
[N+:1]([C:4]1[CH:5]=[C:6]([OH:10])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].C(=O)([O-])[O-].[K+].[K+].S([O-])(=O)(=O)C.[CH2:22]([N:24]([CH:27](O)[CH2:28][CH3:29])[CH2:25][CH3:26])[CH3:23]>CN(C=O)C.O>[CH2:22]([N:24]([CH2:25][CH3:26])[CH2:27][CH2:28][CH2:29][O:10][C:6]1[CH:7]=[CH:8][CH:9]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=1)[CH3:23]

Komponenten

7

Edukt 4

HCID 111373-NitrophenolHCID 11430Potassium CarbonateHCID 85257MethanesulfonateHCID 5256659Diethylamino-propanol

Produkt 1

HCID 22012884N,N-diethyl-N-[3-(3-nitrophenoxy)propyl]amine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel2×

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a stirred solution of 3-nitrophenol (2 mmol) in DMF (6 mL) at rt, solid potassium carbonate (4 mmol) was added. A solution of the mesylate of N,N-diethylaminopropanol (2.2 mmol) in DMF (2 mL) was then added to the reaction mixture and heated to 80° C. until completion, according to General Procedure Q1, as indicated by TLC or HPLC. After cooling to rt, the reaction mixture was then treated with cold H2O (15 mL), and extracted with EtOAc (2×15 mL). The combined organic layers were washed with brine and dried over sodium sulfate. Evaporation of the solvent in vacuuo afforded the desired N,N-diethyl-N-[3-(3-nitrophenoxy)propyl]amine. The crude product was used directly for further transformation.

Aufarbeitung

  1. temperatureAfter cooling to rt
  2. extractionextracted with EtOAc (2×15 mL)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over sodium sulfate
  5. customEvaporation of the solvent in vacuuo

Quellen und Nachweise

ORD-Eintrag
ord-1a59dbac1df94d85990d11a3d8f7174d
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07737285B2

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