Sodium hydride → N-(2-Dimethylaminoethyl)-N-(5-methyl-2-pyridyl)acetamide

HRID 1395523Notes

Reaction equation

HRID 1395523 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9](=[O:11])[CH3:10])=[N:6][CH:7]=1.[H-].[Na+].Cl.[CH3:15][N:16]([CH3:20])[CH2:17][CH2:18]Cl>CN(C)C=O>[CH3:15][N:16]([CH3:20])[CH2:17][CH2:18][N:8]([C:5]1[CH:4]=[CH:3][C:2]([CH3:1])=[CH:7][N:6]=1)[C:9](=[O:11])[CH3:10]

Participants

5

Reactant 3

HCID 24758Sodium hydride2×HCID 818995N-(5-Methyl-2-pyridyl)acetamideHCID 11636816N,N-Dimethylaminoethyl chloride hydrochloride

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N-(5-Methyl-2-pyridyl)acetamide (75.0 g, 0.5 mole) is dissolved in 1000 ml of dry dimethylformamide and a 50% suspension of sodium hydride in mineral oil (24.0 g, 0.5 mole) is added under nitrogen with stirring in two portions over 1/2 hour. The temperature rises to 40° and then is increased to 50°-55° to keep the salt in addition. Additional sodium hydride suspension (28.8 g, 0.6 mole) is added over 10 minutes followed by 2-dimethylaminoethyl chloride hydrochloride (86.5 g, 0.6 mole) added in small portions over 1/2 hour. The temperature is moderated at 70° with occasional ice bath cooling. Then the mixture is stirred overnight at steam bath temperature. The reaction mixture is cooled and filtered. Removal of the dimethylformamide under reduced pressures gives a dark liquid. The product distills as a pale yellow liquid at 124°-128° at 0.6 mm, n25D 1.5216. Weight obtained is 78 g.

Workup

  1. customrises to 40°
  2. temperatureis increased to 50°-55°
  3. additionadded in small portions over 1/2 hour
  4. customThe temperature is moderated at 70° with occasional ice bath
  5. temperaturecooling
  6. stirringThen the mixture is stirred overnight at steam bath temperature
  7. temperatureThe reaction mixture is cooled
  8. filtrationfiltered
  9. customRemoval of the dimethylformamide under reduced pressures
  10. customgives a dark liquid
  11. distillationThe product distills as a pale yellow liquid at 124°-128° at 0.6 mm, n25D 1.5216
  12. customWeight obtained

Sources & evidence

ORD record
ord-5bbb0eba67264db4aa42ad1974d4fb6e
Source dataset
uspto-grants-1980_05
Patent number
US04203988

Reaction notes

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