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

HRID 1154321Notes

Reaction equation

HRID 1154321 reaction equation
[CH:1]([C:3]1[CH:8]=[CH:7][N:6]=[CH:5][CH:4]=1)=[CH2:2].[NH2:9][CH2:10][CH2:11][NH2:12].Cl>CO.O>[N:6]1[CH:7]=[CH:8][C:3]([CH2:1][CH2:2][NH:9][CH2:10][CH2:11][NH2:12])=[CH:4][CH:5]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3301EthylenediamineHCID 75024-Vinylpyridine

Product 1

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

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 962WaterSolvent

Procedure

A solution of 4-vinylpyridine (52.5 g) in methanol (250 cm3) was added dropwise over 2 hours to a stirred solution of 1,2-diaminoethane in methanol (500 cm3) and water (500 cm3) under reflux in the presence of an excess of concentrated hydrochloric acid (pH1). After a further 1.5 hours the mixture was concentrated in vacuo and basified to pH9 with 4M sodium hydroxide solution. The solution was extracted with chloroform (4×150 cm3) and the dried (MgSO4) extracts were evaporated in vacuo to give an oil. Distillation gave N-[2-(4-pyridyl)ethyl]-1,2-diaminoethane as a colourless oil, b.p. 119°-122°/0.09 mm (27.0 g).

Workup

  1. concentrationAfter a further 1.5 hours the mixture was concentrated in vacuo
  2. extractionThe solution was extracted with chloroform (4×150 cm3)
  3. dry with materialthe dried (MgSO4) extracts
  4. customwere evaporated in vacuo
  5. customto give an oil
  6. distillationDistillation

Sources & evidence

ORD record
ord-6b05afab06b24919be2cc4b7e68db8d1
Source dataset
uspto-grants-1984_12
Patent number
US04489075

Reaction notes

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