Potassium Iodide → N,N-dimethyl N'-[2-(3-pyridyl)ethyl]ethanediamine

HRID 1956159Notes

Reaction equation

HRID 1956159 reaction equation
Cl.Cl[CH2:3][CH2:4][C:5]1[CH:6]=[N:7][CH:8]=[CH:9][CH:10]=1.[CH3:11][N:12]([CH3:16])[CH:13]([NH2:15])[CH3:14].C(=O)(O)[O-].[Na+].[I-].[K+]>C(O)C>[CH3:11][N:12]([CH3:16])[CH:13]([NH:15][CH2:3][CH2:4][C:5]1[CH:6]=[N:7][CH:8]=[CH:9][CH:10]=1)[CH3:14]

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 199465Pyridine, 3-(2-chloroethyl)-, hydrochlorideHCID 516892Sodium BicarbonateHCID 18943179N~1~,N~1~-Dimethylethane-1,1-diamine

Product 1

HCID 18788472N,N-dimethyl N'-[2-(3-pyridyl)ethyl]ethanediamineYield 56.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

11 g of 3-(2-chloroethyl)pyridine hydrochloride, 16.3 g of N,N-dimethylethane diamine, 18.5 g of sodium bicarbonate and 13 g of potassium iodide are heated in 150 ml of ethanol for about 30 hours at about 60° C. The solvent is evaporated and the residue is taken up in 100 ml of water before an aqueous solution of 10N NaOH is added to give pH 8; the aqueous phase is then extracted 3 times with 80 ml of ethyl acetate. The pooled organic phases are dried over magnesium sulfate, filtered and concentrated under reduced pressure. The residual oil is distilled to give 6.7 g of the expected product. B.p.=100°-107° C./10 Pa.

Workup

  1. customThe solvent is evaporated
  2. additionis added
  3. customto give pH 8
  4. extractionthe aqueous phase is then extracted 3 times with 80 ml of ethyl acetate
  5. dry with materialThe pooled organic phases are dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. distillationThe residual oil is distilled

Sources & evidence

ORD record
ord-708ad11e145040bca2bbd0e00e7ebf5d
Source dataset
uspto-grants-1998_07
Patent number
US05780468

Reaction notes

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