Hydrochloric Acid → 4-[2-(2-Nitrophenoxy)ethyl]morpholine

HRID 885923Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 885923
[OH:1][CH2:2][CH2:3][N:4]1[CH2:9][CH2:8][O:7][CH2:6][CH2:5]1.[H-].[Na+].F[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[N+:19]([O-:21])=[O:20].Cl>CN(C=O)C>[N+:19]([C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=1[O:1][CH2:2][CH2:3][N:4]1[CH2:9][CH2:8][O:7][CH2:6][CH2:5]1)([O-:21])=[O:20]

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 611632-MorpholinoethanolHCID 738951-Fluoro-2-nitrobenzene

Produkt 1

HCID 8673614-[2-(2-Nitrophenoxy)ethyl]morpholineAusbeute 90 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

To a stirred solution of 4-(2-hydroxyethyl)morpholine (1.7 g, 12.96 mmol) in DMF (2 mL) was added NaH (0.52 g, 60% dispersion in oil, 12.96 mmol). The reaction mixture was stirred at r.t. for 10 minutes, then cooled to 0° C. A solution of 2-fluoronitrobenzene (1.5 g, 10.63 mmol) in DMF (2 mL) was added over 5 min. The reaction mixture was allowed to warm to r.t., then was stirred for 2 h before the addition of 2M aqueous HCl (50 mL). The aqueous fraction was separated, neutralised with aqueous sat. NaHCO3 and extracted with EtOAc (2×50 mL). The combined organic fractions were dried (Na2SO4), filtered and concentrated in vacuo to give the title compound (2.4 g, 90%) as a yellow oil that was used without further purification. LCMS (ES+) 253.0 (M+H)+, RT 2.06 minutes (Method 5).

Aufarbeitung

  1. temperaturecooled to 0° C
  2. temperatureto warm to r.t.
  3. customThe aqueous fraction was separated
  4. extractionextracted with EtOAc (2×50 mL)
  5. dry with materialThe combined organic fractions were dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-725ce74c8ce045e3a6b425bb7c292a62
Quelldatensatz
uspto-grants-2012_08
Patentnummer
US08242116B2

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