Diethyl Ether → 2,2-Dimethyl-3-(pyridin-4-yl)propan-1-amine

HRID 1393161

Reaktionsgleichung

Reaktionsgleichung von HRID 1393161
C(OCC)C.[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:12][C:13]([CH3:34])([CH:16]([C:28]1[CH:33]=[CH:32][N:31]=[CH:30][CH:29]=1)OS(C1C=CC(C)=CC=1)(=O)=O)[C:14]#[N:15].[OH-].[Na+]>O1CCCC1.O>[CH3:12][C:13]([CH3:34])([CH2:16][C:28]1[CH:33]=[CH:32][N:31]=[CH:30][CH:29]=1)[CH2:14][NH2:15]

Komponenten

7

Edukt 4

HCID 3283Diethyl EtherHCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 219740222,2-Dimethyl-3-(4-pyridyl)-3-(p-tolylsulfonyloxy)propionitrile

Produkt 1

HCID 121366422,2-Dimethyl-3-(pyridin-4-yl)propan-1-amineAusbeute 28 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittel2×HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Anhydrous diethyl ether (10 ml) was dropwise to lithium aluminum hydride (345 mg, 9.10 mmol) under a nitrogen atmosphere and ice-cold water-cooling. Then, a solution of 2,2-dimethyl-3-(4-pyridyl)-3-(p-tolylsulfonyloxy)propionitrile (600 mg, 1.82 mmol) in tetrahydrofuran (10 ml) was added dropwise to the mixture. The whole was stirred at room temperature overnight, and water (324 μl), a 15% aqueous sodium hydroxide solution (324 μl) and water (972 μl) were added successively to the reaction mixture while stirring it vigorously under ice-cold water-cooling. The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure, and the concentrate was purified by silica gel column chromatography to give the titled compound (83.0 mg, 0.505 mmol, 28%) as a pale yellow oily matter.

Aufarbeitung

  1. temperatureice-cold water-cooling
  2. stirringwhile stirring it vigorously under ice-cold water-
  3. temperaturecooling
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customthe concentrate was purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-5854762690a14f08a0b2ece6c92b5f24
Quelldatensatz
uspto-grants-2008_03
Patentnummer
US07345064B2

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