Pyridine → N~2~-(6-Chloropyridin-2-yl)-N~1~,N~1~-dimethylethane-1,2-diamine

HRID 1395530Notes

Reaction equation

HRID 1395530 reaction equation
Cl[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[N:3]=1.C[NH:10][CH2:11][CH2:12][NH:13][CH3:14].N1C=CC=C[CH:16]=1>>[CH3:16][N:13]([CH3:14])[CH2:12][CH2:11][NH:10][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[N:3]=1

Participants

4

Reactant 3

HCID 1049PyridineHCID 8070N,N'-DimethylethylenediamineHCID 169892,6-Dichloropyridine

Product 1

HCID 20339561N~2~-(6-Chloropyridin-2-yl)-N~1~,N~1~-dimethylethane-1,2-diamineYield 70%

Procedure

A solution of 2,6-dichloropyridine (29.6 g., 0.20 mole) and unsymmetrical dimethylethylenediamine (52.9 g., 0.60 mole) in 100 ml of pyridine is stirred at reflux for 48 hours. The pyridine is removed under reduced pressure and the residual mixture is poured into water and made basic with excess sodium hydroxide. The product is extracted into ethyl acetate which is then concentrated and the residual oil is distilled. 2-(2-Dimethylaminoethylamino)-6-chloropyridine boiling at 104°-105° at 0.2 mm is collected in 70% yield.

Workup

  1. temperatureat reflux for 48 hours
  2. customThe pyridine is removed under reduced pressure
  3. additionthe residual mixture is poured into water
  4. extractionThe product is extracted into ethyl acetate which
  5. concentrationis then concentrated
  6. distillationthe residual oil is distilled
  7. custom2-(2-Dimethylaminoethylamino)-6-chloropyridine boiling at 104°-105° at 0.2 mm is collected in 70% yield

Sources & evidence

ORD record
ord-3aad83be6d564b87924b3fa512e8ba83
Source dataset
uspto-grants-1980_05
Patent number
US04203988

Reaction notes

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