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

HRID 2075884Notes

Reaction equation

HRID 2075884 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, the temperature was raised to room temperature, and the whole was stirred 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 0.15 g (75%) of the titled compound as a pale yellow oily matter.

Workup

  1. temperaturecooling
  2. stirringthe whole was stirred 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-125eac854de6440fb2cd2639293430c2
Source dataset
uspto-grants-2011_04
Patent number
US07923461B2

Reaction notes

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