Morpholine → 4-(5-Morpholino-3-nitropyridin-2-yl)morpholine

HRID 1431379Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1431379
Cl[C:2]1[CH:3]=[C:4]([N+:14]([O-:16])=[O:15])[C:5]([N:8]2[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)=[N:6][CH:7]=1.[NH:17]1[CH2:22][CH2:21][O:20][CH2:19][CH2:18]1.C1(P(C2CCCCC2)C2(C(C)C)CC(C(C)C)=CC(C(C)C)=C2C2C=CC=CC=2)CCCCC1.CC(C)([O-])C.[Na+]>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd]>[O:11]1[CH2:12][CH2:13][N:8]([C:5]2[N:6]=[CH:7][C:2]([N:17]3[CH2:22][CH2:21][O:20][CH2:19][CH2:18]3)=[CH:3][C:4]=2[N+:14]([O-:16])=[O:15])[CH2:9][CH2:10]1

Komponenten

7

Edukt 4

HCID 8083MorpholineHCID 23676156Sodium t-butoxideHCID 596312064-(5-Chloro-3-nitropyridin-2-yl)morpholineHCID 672859322-Dicyclohexylphosphino-2,4,6-triisopropylbiphenyl

Produkt 1

HCID 596312774-(5-Morpholino-3-nitropyridin-2-yl)morpholine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6505921(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladiumKatalysatorHCID 1140TolueneLösungsmittel

Versuchsvorschrift

To a stirred solution of 4-(5-chloro-3-nitropyridin-2-yl)morpholine (2.48 g, 10 mmol; described herein) in toluene (190 mL) were sequentially added morpholine (1.8 mL, 20 mmol), tris(dibenzylideneacetone)dipalladium(o) (0.65 g, 0.71 mmol), 2-(dicyclohexylphosphino)-2,4,6,-tri-i-propyl-1,1-biphenyl (0.73 g, 1.5 mmol), and sodium tert-butoxide (2.0 g, 20 mmol). The reaction was heated to reflux overnight, cooled to rt, and concentrated. The resulting residue was taken up in EtOAc, washed with satd aq. sodium bicarbonate solution and brine, and the organic layer dried (magnesium sulfate) and concentrated. Column chromatography afforded 4-(6-morpholino-5-nitropyridin-3-yl)morpholine as a red oil. Mass Spectrum (ESI) m/e=295.1 (M+1).

Aufarbeitung

  1. temperatureThe reaction was heated
  2. temperatureto reflux overnight
  3. concentrationconcentrated
  4. washwashed with satd aq. sodium bicarbonate solution and brine
  5. dry with materialthe organic layer dried (magnesium sulfate)
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-131aa12eec73447c943a8e72586d910e
Quelldatensatz
uspto-grants-2015_01
Patentnummer
US08940724B2

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