Ethylenediamine → 1,2-Ethanediamine, N-[2-(4-pyridinyl)ethyl]-

HRID 364612Notes

Reaction equation

HRID 364612 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([CH2:7][CH2:8]C(N)CN)=[CH:3][CH:2]=1.[CH2:13]([NH2:16])[CH2:14][NH2:15]>>[N:1]1[CH:2]=[CH:3][C:4]([CH2:7][CH2:8][NH:15][CH2:14][CH2:13][NH2:16])=[CH:5][CH:6]=1

Participants

3

Reactant 2

HCID 3301EthylenediamineHCID 131714825HCID 131714825, compound

Product 1

HCID 73304671,2-Ethanediamine, N-[2-(4-pyridinyl)ethyl]-Yield 35%

Procedure

This was an adaptation of the procedure reported by R. G. Lacoste and A. E. Martel in Inorganic Chemistry 1964, 3(6), 881, for the preparation of N-[2-(4-pyridyl-ethyl]ethylene diamine. To a 250 ml three neck round bottom flask, fitted with a dropping funnel, a reflux condenser, and magnetic stirring, was added 12.02 g (0.2 mol) ethylene diamine, 24 g distilled water, and 31.50 g (0.3 mol) freshly distilled 4-vinylpyridine. The temperature was maintained at 20°-30° C. while 12.0 g glacial acetic was added through the dropping funnel. After all the acetic acid was added, the reaction mixture was heated on the steam bath for two hours. The product was fractionally distilled to give 11.48 g (35% yield). The product was characterized by IR and NMR.

Workup

  1. distillationdistilled water, and 31.50 g (0.3 mol) freshly distilled 4-vinylpyridine
  2. temperatureThe temperature was maintained at 20°-30° C. while 12.0 g glacial acetic
  3. additionwas added through the dropping funnel
  4. additionAfter all the acetic acid was added
  5. temperaturethe reaction mixture was heated on the steam bath for two hours
  6. distillationThe product was fractionally distilled
  7. customto give 11.48 g (35% yield)

Sources & evidence

ORD record
ord-615a31e835b74f3b9d5bd10af8be878f
Source dataset
uspto-grants-1986_08
Patent number
US04605607

Reaction notes

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