Water → 4-(Pyridin-2-yl)butan-1-amine

HRID 2419038Notes

Reaction equation

HRID 2419038 reaction equation
[C:1]([CH2:3][CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][N:7]=1)#[N:2].[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>CCOCC>[NH2:2][CH2:1][CH2:3][CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][N:7]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 150322564-(Pyridin-2-yl)butanenitrileHCID 21226445Aluminium lithium hydride

Product 1

HCID 135110834-(Pyridin-2-yl)butan-1-amineYield 44.7%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

2-(3-cyanopropyl)pyridine (14.6 g) in dry ether (100 ml) is added dropwise to a stirred suspension of lithium aluminium hydride (9.5 g) in dry ether (300 ml). The mixture is heated under reflux for 3 hours, cooled and treated successively with water, aqueous sodium hydroxide and water. Extraction with chloroform, followed by fractionation affords 2-(4-aminobutyl)pyridine (6.7 g), b.p. 100°-101° C./1.0 mm.

Workup

  1. temperatureThe mixture is heated
  2. temperatureunder reflux for 3 hours
  3. temperaturecooled
  4. extractionExtraction with chloroform

Sources & evidence

ORD record
ord-acbd0e9ad9d5418c8a540e38b836c481
Source dataset
uspto-grants-1978_08
Patent number
US04104382

Reaction notes

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