Water → 2-(Pyridin-3-yl)ethan-1-amine

HRID 850465Notes

Reaction equation

HRID 850465 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[N:7]1[CH:12]=[CH:11][CH:10]=[C:9]([CH2:13][C:14]#[N:15])[CH:8]=1.O.[OH-].[Na+]>C(OCC)C>[N:7]1[CH:12]=[CH:11][CH:10]=[C:9]([CH2:13][CH2:14][NH2:15])[CH:8]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 809233-PyridineacetonitrileHCID 21226445Aluminium lithium hydride

Product 1

HCID 8540512-(Pyridin-3-yl)ethan-1-amineYield 39.1%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

LAH (1.90 g, 50 mmol) was suspended in diethyl ether (150 ml), and a solution of 3-pyridylacetonitrile (5.91 g, 50 mmol, 1.0 eq) in diethyl ether (150 ml) was added at room temperature. The mixure was stirred at room temperature for 14 hours. To this reaction mixture were successively added water (1.9 ml), a 15% aqueous sodium hydroxide solution (1.9 ml) and water (5.7 ml). The resulting precipitate was filtered through Celite and washed with diethyl ether, which was followed by concentration under reduced pressure. The obtained residue was subjected to column chromatography (chloroform/methanol=30/1-chloroform/methanol/triethylamine=8/2/0.1) to give 2-(3-pyridyl)ethylamine (2.39 g, 39%) as a colorless oil.

Workup

  1. filtrationThe resulting precipitate was filtered through Celite
  2. washwashed with diethyl ether, which
  3. concentrationwas followed by concentration under reduced pressure

Sources & evidence

ORD record
ord-4d8b0cbf41e64008a4a4c39216ccd388
Source dataset
uspto-grants-2000_01
Patent number
US06017919

Reaction notes

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