N,N'-Dimethylethylenediamine → HCID 19992421, compound

HRID 345441Notes

Reaction equation

HRID 345441 reaction equation
Cl.Cl[C:3]1[CH:8]=[CH:7][N:6]=[CH:5][CH:4]=1.[CH3:9][NH:10][CH2:11][CH2:12][NH:13][CH3:14].C(=O)(O)[O-].[Na+]>C(O)CC(C)C>[CH3:9][N:10]([C:3]1[CH:8]=[CH:7][N:6]=[CH:5][CH:4]=1)[CH2:11][CH2:12][NH:13][CH3:14]

Participants

5

Reactant 3

HCID 8070N,N'-DimethylethylenediamineHCID 818524-Chloropyridine hydrochlorideHCID 516892Sodium Bicarbonate

Product 1

HCID 19992421HCID 19992421, compoundYield 50.2%

Reagents, catalysts & solvents 1

HCID 31260Isoamyl AlcoholSolvent

Procedure

A mixture of 4-chloropyridine hydrochloride (15.0 g), N,N'-dimethyl-1,2-ethanediamine (22.0 g) and sodium bicarbonate (25.20 g) in isoamyl alcohol (100 ml) was heated under reflux for 48 hours and then evaporated. The residue was extracted several times with hot dichloromethane and the combined extracts were filtered and evaporated. The residue was distilled to give the product (8.30 g), b.p. 168°-172° @ 15 mm.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 48 hours
  3. customevaporated
  4. extractionThe residue was extracted several times with hot dichloromethane
  5. filtrationthe combined extracts were filtered
  6. customevaporated
  7. distillationThe residue was distilled

Sources & evidence

ORD record
ord-554d03c9a7d84cccbb8886988ad871f6
Source dataset
uspto-grants-1991_10
Patent number
US05057528

Reaction notes

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