Water → 4-(Pyridin-3-yloxy)butan-1-amine

HRID 745515Notes

Reaction equation

HRID 745515 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[N:7]1[CH:12]=[CH:11][CH:10]=[C:9]([O:13][CH2:14][CH2:15][CH2:16][C:17]#[N:18])[CH:8]=1.O.[OH-].[Na+]>CCOCC.C1COCC1>[N:7]1[CH:12]=[CH:11][CH:10]=[C:9]([O:13][CH2:14][CH2:15][CH2:16][CH2:17][NH2:18])[CH:8]=1

Participants

7

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 137117804-(3-Pyridinyloxy)butyronitrileHCID 21226445Aluminium lithium hydride

Product 1

HCID 121122194-(Pyridin-3-yloxy)butan-1-amineYield 53%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To 2.9 g (0.073 mol) of lithium aluminum hydride stirred at 25° in 100 ml of anhydrous ether at 25° was added dropwise 4.7 g (0.029 mol) of 4-(3-pyridinyloxy)butyronitrile in 30 ml of ether and 20 ml anhydrous THF over 15 minutes. The reaction mixture was then stirred at reflux for 3.5 hours, cooled in an ice bath during the addition of 3 ml of H2O, followed by 3 ml of 15% NaOH solution and finally 9 ml of H2O. The granular solid was filtered, washed with CHCl3 and the filtrate was concentrated in vacuo. The residue was dissolved in CHCl3, washed with H2O, dried (MgSO4) and concentrated in vacuo to an oil. Distillation gave 2.6 g., b.p. 103°-107°/0.5 mm (53% yield) of the desired amine which was analyzed as the dihydrochloride obtained from 2-propanol-ether, m.p. 127°-131° .

Workup

  1. temperatureat reflux for 3.5 hours
  2. filtrationThe granular solid was filtered
  3. washwashed with CHCl3
  4. concentrationthe filtrate was concentrated in vacuo
  5. dissolutionThe residue was dissolved in CHCl3
  6. washwashed with H2O
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated in vacuo to an oil
  9. distillationDistillation
  10. customgave 2.6 g

Sources & evidence

ORD record
ord-3e2a13ea375a4e02914cd6130f5dcfdf
Source dataset
uspto-grants-1986_07
Patent number
US04599336

Reaction notes

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