Sodium Hydroxide → N-{2,5-Dimethyl-4-[2-(morpholin-4-yl)ethoxy]phenyl}acetamide

HRID 1822899

Reaktionsgleichung

Reaktionsgleichung von HRID 1822899
[OH:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([NH:9][C:10](=[O:12])[CH3:11])=[C:4]([CH3:13])[CH:3]=1.Cl.Cl[CH2:16][CH2:17][N:18]1[CH2:23][CH2:22][O:21][CH2:20][CH2:19]1.[OH-].[Na+]>O1CCOCC1>[CH3:13][C:4]1[CH:3]=[C:2]([O:1][CH2:16][CH2:17][N:18]2[CH2:23][CH2:22][O:21][CH2:20][CH2:19]2)[C:7]([CH3:8])=[CH:6][C:5]=1[NH:9][C:10](=[O:12])[CH3:11]

Komponenten

5

Edukt 3

HCID 14798Sodium HydroxideHCID 77210Morpholine, 4-(2-chloroethyl)-, hydrochloride (1:1)HCID 155307Acetamide, N-(4-hydroxy-2,5-dimethylphenyl)-

Produkt 1

HCID 22169683N-{2,5-Dimethyl-4-[2-(morpholin-4-yl)ethoxy]phenyl}acetamideAusbeute 89 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

To a suspension of N-(4-hydroxy-2,5-dimethyl-phenyl)-acetamide (8.0 g, 44.6 mmol) and 4-(2-chloro-ethyl)-morpholine hydochloride (9.97 g, 53.6 mmol) in 50 mL of dioxane was added a solution of NaOH (4.29 g in 50 mL of water). The mixture was refluxed for 2 h and evaporated to dryness under reduced pressure. The residue was dissolved in CH2Cl2 and washed with 0.5 N NaOH. The organic phase was dried (Na2SO4), evaporated, and crystallized from CH2Cl2-hexane to give N-[2,5-dimethyl-4-(2-morpholin-4-yl-ethoxy)-phenyl]-acetamide as gray solid (11.6 g, 89%).

Aufarbeitung

  1. temperatureThe mixture was refluxed for 2 h
  2. customevaporated to dryness under reduced pressure
  3. dissolutionThe residue was dissolved in CH2Cl2
  4. washwashed with 0.5 N NaOH
  5. dry with materialThe organic phase was dried (Na2SO4)
  6. customevaporated
  7. customcrystallized from CH2Cl2-hexane

Quellen und Nachweise

ORD-Eintrag
ord-30f721b44e784b27b28ba95c5d40e765
Quelldatensatz
uspto-grants-2006_05
Patentnummer
US07037909B2

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