Water → 4-[1-(Diphenylmethyl)azetidin-3-yl]morpholine

HRID 1599436Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1599436
[C:1]1([CH:7]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[N:8]2[CH2:11][CH:10](OS(C)(=O)=O)[CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(=O)([O-])[O-].[K+].[K+].[NH:29]1[CH2:34][CH2:33][O:32][CH2:31][CH2:30]1.O>C(#N)C>[C:1]1([CH:7]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[N:8]2[CH2:11][CH:10]([N:29]3[CH2:34][CH2:33][O:32][CH2:31][CH2:30]3)[CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 8083MorpholineHCID 11430Potassium CarbonateHCID 27587161-(Diphenylmethyl)azetidin-3-yl methanesulfonate

Produkt 1

HCID 211837864-[1-(Diphenylmethyl)azetidin-3-yl]morpholineAusbeute 693 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A solution of 1-diphenylmethyl-3-methanesulphonyloxyazetidine (Preparation 1(b)) (24.46 g, 7.72 mmol), potassium carbonate (32 g, 3 mol equiv) and morpholine (7.34 ml, 1.09 mol equiv) in acetonitrile (200 ml) was heated under reflux for 4 hours. The solution was then cooled to room temperature, water (50 ml) added and the mixture concentrated in vacuo. The residue was then partitioned between ethyl acetate (400 ml) and water (400 ml) and the organic phase washed with water (2×400 ml). The organic phase was dried over MgSO4, and the solvent removed in vacuo. The residue was chromatographed using silica gel eluting with hexane: diethyl ether (1:1) to give the title compound (16.5 g).

Aufarbeitung

  1. temperatureunder reflux for 4 hours
  2. concentrationthe mixture concentrated in vacuo
  3. customThe residue was then partitioned between ethyl acetate (400 ml) and water (400 ml)
  4. washthe organic phase washed with water (2×400 ml)
  5. dry with materialThe organic phase was dried over MgSO4
  6. customthe solvent removed in vacuo
  7. customThe residue was chromatographed

Quellen und Nachweise

ORD-Eintrag
ord-af374f2bbc114b0a9380dd58743c6079
Quelldatensatz
uspto-grants-1998_04
Patentnummer
US05741790

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