Diethyl Ether → 3-(Pyridin-4-yl)butan-1-amine

HRID 18392Notes

Reaction equation

HRID 18392 reaction equation
CCOCC.[H-].[Al+3].[Li+].[H-].[H-].[H-].[N:12]1[CH:17]=[CH:16][C:15]([CH:18]([CH3:23])[CH2:19][C:20]([NH2:22])=O)=[CH:14][CH:13]=1.[OH-].[Na+]>C(Cl)Cl.C(OCC)(=O)C>[N:12]1[CH:17]=[CH:16][C:15]([CH:18]([CH3:23])[CH2:19][CH2:20][NH2:22])=[CH:14][CH:13]=1

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 21973937HCID 21973937, compound

Product 1

HCID 147508173-(Pyridin-4-yl)butan-1-amineYield 75%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Next, anhydrous ether (8 ml) was added to lithium aluminum hydride (0.16 g, 4.2 mmol) under a nitrogen atmosphere, and the mixture was stirred under ice-cooling. A solution of 3-(4-pyridyl)butyramide (0.22 g, 1.4 mmol) in anhydrous methylene chloride (8 ml) was added dropwise to the mixture over two minutes, and then the whole was stirred at room temperature overnight. Ethyl acetate (1 ml) and a 1 N aqueous sodium hydroxide solution (20 ml) were added to the reaction mixture, and the whole was extracted with chloroform (50 ml). The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to give the target compound (0.15 g, 75%) as a pale yellow oily matter.

Workup

  1. temperaturecooling
  2. stirringthe whole was stirred at room temperature overnight
  3. extractionthe whole was extracted with chloroform (50 ml)
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-31c19101808a4268bc554d5931442f5b
Source dataset
uspto-grants-2010_06
Patent number
US07741346B2

Reaction notes

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