Water → 4-(Pyridin-4-yl)butan-1-amine

HRID 1719998Notes

Reaction equation

HRID 1719998 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([CH2:7][CH2:8][CH2:9][C:10]#[N:11])=[CH:3][CH:2]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>O1CCCC1>[N:1]1[CH:6]=[CH:5][C:4]([CH2:7][CH2:8][CH2:9][CH2:10][NH2:11])=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 135575314-(Pyridin-4-YL)butanenitrileHCID 21226445Aluminium lithium hydride

Product 1

HCID 135575324-(Pyridin-4-yl)butan-1-amineYield 6.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
10 °C

Procedure

The title product of Example 22(5.0 g, 34.0 mmol) in 40 mL of tetrahydrofuran was added dropwise to a stirred suspension of lithium aluminum hydride (LiAlH4, 3.2 g, 85.0 mmol) in 100 mL of THF over 20 minutes. The reaction was brought to reflux for 2 hours, cooled to 10° C., and treated with water (33.2 mL), 15% NaOH (3.2 mL), and then water (9.6 mL) again. The mixture was filtered and the solid was washed with Et2O. The filtrate was dried (Na2SO4), filtered, and stripped of solvent to yield 4.0 g of crude product that was distilled to produce the title compound (340 mg).

Workup

  1. temperatureto reflux for 2 hours
  2. filtrationThe mixture was filtered
  3. washthe solid was washed with Et2O
  4. dry with materialThe filtrate was dried (Na2SO4)
  5. filtrationfiltered
  6. customto yield 4.0 g of crude product that
  7. distillationwas distilled

Sources & evidence

ORD record
ord-087111dc711f4f2c9f03488b123f389f
Source dataset
uspto-grants-1996_04
Patent number
US05504077

Reaction notes

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