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

HRID 18397

Reaction equation

HRID 18397 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].C(OCC)C.[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

Lithium aluminum hydride (345 mg, 9.10 mmol) was put under a nitrogen atmosphere, and anhydrous diethyl ether (10 ml) was added dropwise thereto under ice-cold water-cooling. Next, 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 under ice-cold water-cooling while stirring it vigorously. The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure, and the obtained concentrate was purified by silica gel column chromatography to give the target compound (83.0 mg, 0.505 mmol, 28%) as a pale yellow oily matter.

Workup

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

Sources & evidence

ORD record
ord-4eb857f5e3144afe9cd71d3fb2559940
Source dataset
uspto-grants-2010_06
Patent number
US07741346B2

Linked notes

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