4-Methylmorpholine → N-[4-(4-Hydroxy-phenoxy)-benzyl]-propionamide

HRID 49152

Reaktionsgleichung

Reaktionsgleichung von HRID 49152
[NH2:1][CH2:2][C:3]1[CH:16]=[CH:15][C:6]([O:7][C:8]2[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=2)=[CH:5][CH:4]=1.CN1CCOCC1.[C:24](Cl)(=[O:27])[CH2:25][CH3:26]>C(#N)C>[OH:14][C:11]1[CH:12]=[CH:13][C:8]([O:7][C:6]2[CH:15]=[CH:16][C:3]([CH2:2][NH:1][C:24](=[O:27])[CH2:25][CH3:26])=[CH:4][CH:5]=2)=[CH:9][CH:10]=1

Komponenten

5

Edukt 3

HCID 79724-MethylmorpholineHCID 62324Propionyl chlorideHCID 20636236HCID 20636236, Verbindung

Produkt 1

HCID 20636237N-[4-(4-Hydroxy-phenoxy)-benzyl]-propionamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A mixture of 4-(4-Aminomethyl-phenoxy)-phenol (0.10 g, 0.47 mmol), MMP-resin (polystyrene bound N-methylmorpholine-type base, 0.30 g, 1.04 mmol) and 1.9 mL of acetonitrile was treated with propionyl chloride (0.086 mL, 1.0 mmol) and shaken for 24 hours at room temperature. After filtration of the resin, the filtrate was diluted with 2 mL of methanol and was treated with 2 mL of 1M lithium hydroxide (LiOH) in water. The mixture was shaken for 24 hours at room temperature, treated with Amberlite IRP-64® resin until neutral, filtered and concentrated in vacuo, affording N-[4-(4-Hydroxy-phenoxy)-benzyl]-propionamide. MS (m/z): 272.2 [M+H]+.

Aufarbeitung

  1. filtrationAfter filtration of the resin
  2. additionthe filtrate was diluted with 2 mL of methanol
  3. additionwas treated with 2 mL of 1M lithium hydroxide (LiOH) in water
  4. stirringThe mixture was shaken for 24 hours at room temperature
  5. additiontreated with Amberlite IRP-64® resin until neutral,
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-75350c41cd7e499796319afe0614f444
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06706723B2

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