Triethylamine → 4-(Pyridin-4-yl)butan-1-amine

HRID 1583400Notes

Reaction equation

HRID 1583400 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.C(N(CC)CC)C.[H][H]>C(O)C.[Co]>[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 3

HCID 8471TriethylamineHCID 135575314-(Pyridin-4-YL)butanenitrileHCID 178418361HCID 178418361, compound

Product 1

HCID 135575324-(Pyridin-4-yl)butan-1-amineYield 31.5%

Reagents, catalysts & solvents 2

HCID 104730CobaltCatalystHCID 702EthanolSolvent

Procedure

A solution of 30.0 g of 4-pyridinebutanenitrile in 200 ml of ethanol containing 7.5 ml of triethylamine was hydrogenated over 7.5 g of Raney cobalt at 100° C. and 1200 lbs. hydrogen pressure. The crude product obtained after filtration and concentration, was distilled to give 9.7 g (31%) of 4-pyridinebutanamine, bp 105°-112° C./0.8 mm. A second fraction (15.3 g, bp 112°-122° C.) consisted of a mixture by thin layer chromatography and was redistilled to give 4.74 g (15%) of 4-pyridinebutanamine, bp 95°-98° C./0.15 mm. The product was further characterized as the hydrochloride salt, mp 124°-125° C. (ethanolether).

Workup

  1. customThe crude product obtained
  2. filtrationafter filtration and concentration
  3. distillationwas distilled

Sources & evidence

ORD record
ord-c0699f02252f48b191c6ba2923693679
Source dataset
uspto-grants-1985_11
Patent number
US04551460

Reaction notes

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