N-(2-Dimethylaminoethyl)-N-(5-methyl-2-pyridyl)acetamide → 2-(2-Dimethylaminoethylamino)-5-methylpyridine

HRID 1395524Notes

Reaction equation

HRID 1395524 reaction equation
[CH3:1][N:2]([CH3:16])[CH2:3][CH2:4][N:5]([C:9]1[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][N:10]=1)C(=O)C>[OH-].[Na+]>[CH3:1][N:2]([CH3:16])[CH2:3][CH2:4][NH:5][C:9]1[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][N:10]=1

Participants

3

Reactant 1

HCID 20339535N-(2-Dimethylaminoethyl)-N-(5-methyl-2-pyridyl)acetamide

Product 1

HCID 203395792-(2-Dimethylaminoethylamino)-5-methylpyridine

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

To N-(2-dimethylaminoethyl)-N-(5-methyl-2-pyridyl) acetamide (50.0 g, 0.226 mole) is added 200 ml of 5 N sodium hydroxide. The mixture is stirred rapidly at reflux for 16 hours. The mixture is cooled and the oil is extracted into ether. The ether extract is dried and evaporated under reduced pressure. Distillation of the residue gives a pale yellow liquid, b.p. 105°-112°, n25D 1.5355. Weight obtained is 35 g.

Workup

  1. temperatureat reflux for 16 hours
  2. temperatureThe mixture is cooled
  3. extractionthe oil is extracted into ether
  4. extractionThe ether extract
  5. customis dried
  6. customevaporated under reduced pressure
  7. distillationDistillation of the residue
  8. customgives a pale yellow liquid, b.p. 105°-112°, n25D 1.5355
  9. customWeight obtained

Sources & evidence

ORD record
ord-1718d04284554ea89fa4944c7c42e1c9
Source dataset
uspto-grants-1980_05
Patent number
US04203988

Reaction notes

Loading…