Ethylenediamine → N1-(pyridin-4-yl)ethane-1,2-diamine

HRID 614365

Reaction equation

HRID 614365 reaction equation
Cl.Br[C:3]1[CH:8]=[CH:7][N:6]=[CH:5][CH:4]=1.[CH2:9]([NH2:12])[CH2:10][NH2:11]>>[NH2:11][CH2:10][CH2:9][NH:12][C:3]1[CH:8]=[CH:7][N:6]=[CH:5][CH:4]=1

Participants

3

Reactant 2

HCID 3301EthylenediamineHCID 881004-Bromopyridinium chloride

Product 1

HCID 14834209N1-(pyridin-4-yl)ethane-1,2-diamine

Procedure

A mixture of 38.9 g of 4-bromo-pyridine-hydrochloride and 480 g of ethylenediamine is refluxed with stirring for 13 hours. The reaction mixture is thereafter concentrated under reduced pressure and the residue is treated with toluene and concentrated once more. The residue is made alkaline with a concentrated aqueous solution of sodium hydroxide and extracted with five 75 ml portions of methylene chloride. The combined extracts are dried over sodium sulphate and concentrated under reduced pressure. Recrystallisation of the residue from methylene chloride yields 4-(2-aminoethylamino)-pyridine as a light yellow crystalline substance with a melting point of 120°-121° C.

Workup

  1. temperatureis refluxed
  2. concentrationThe reaction mixture is thereafter concentrated under reduced pressure
  3. additionthe residue is treated with toluene
  4. concentrationconcentrated once more
  5. extractionextracted with five 75 ml portions of methylene chloride
  6. dry with materialThe combined extracts are dried over sodium sulphate
  7. concentrationconcentrated under reduced pressure
  8. customRecrystallisation of the residue from methylene chloride

Sources & evidence

ORD record
ord-5b5683f49b9c4128b6fd1fc128486bcb
Source dataset
uspto-grants-1979_03
Patent number
US04144344

Linked notes

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