4-Aminophenol → 4-(2-Morpholinoethoxy)aniline

HRID 409655

Reaktionsgleichung

Reaktionsgleichung von HRID 409655
Cl.Cl[CH2:3][CH2:4][N:5]1[CH2:10][CH2:9][O:8][CH2:7][CH2:6]1.[NH2:11][C:12]1[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=1.[OH-].[Na+]>CN(C=O)C>[N:5]1([CH2:4][CH2:3][O:18][C:15]2[CH:16]=[CH:17][C:12]([NH2:11])=[CH:13][CH:14]=2)[CH2:10][CH2:9][O:8][CH2:7][CH2:6]1

Komponenten

5

Edukt 3

HCID 4034-AminophenolHCID 14798Sodium HydroxideHCID 77210Morpholine, 4-(2-chloroethyl)-, hydrochloride (1:1)

Produkt 1

HCID 64847114-(2-Morpholinoethoxy)aniline

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

4-(2-Chloro-ethyl)-morpholine hydrochloride (4.2 g, 22 mmol, 1.2 equiv) is added in one portion to a mixture of 4-aminophenol (2 g, 18.3 mmol) and finely powdered sodium hydroxide (1.87 g, 45.8 mmol, 2.5 equiv) in DMF (32 mL), under an argon atmosphere. The reaction mixture is stirred for 23.5 h at RT. The resulting dark suspension is filtered. The filtrate is diluted with DCM (200 ml) and washed with brine (2×60 mL). The organic phase is dried (sodium sulfate), filtered and concentrated. Purification of the residue by silica gel column chromatography (DCM/EtOH, 95:5→7:3) provides the title compound as a yellow-brown solid: API-MS: 223.2 [MH]+; TLC: Rf=0.31 (DCM/EtOH, 9:1).

Aufarbeitung

  1. filtrationThe resulting dark suspension is filtered
  2. additionThe filtrate is diluted with DCM (200 ml)
  3. washwashed with brine (2×60 mL)
  4. dry with materialThe organic phase is dried (sodium sulfate)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification of the residue by silica gel column chromatography (DCM/EtOH, 95:5→7:3)

Quellen und Nachweise

ORD-Eintrag
ord-9031264226a141c2b99b317bd5426e8b
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08759517B2

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