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

HRID 11457Notes

Reaction equation

HRID 11457 reaction equation
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]

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-46d8f288066544dda525fefef5f195a2
Source dataset
uspto-grants-2006_08
Patent number
US07098226B2

Reaction notes

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