Sodium Hydroxide → p-N,N-dimethylaminoethylpropiophenone

HRID 1980805Notes

Reaction equation

HRID 1980805 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[CH3:5][N:6]([CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[CH3:7].[C:16](Cl)(=[O:19])[CH2:17][CH3:18].[OH-].[Na+]>C(=S)=S.O>[CH3:5][N:6]([CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([C:16](=[O:19])[CH2:17][CH3:18])=[CH:12][CH:11]=1)[CH3:7]

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 25125N,N-DimethylphenylethylamineHCID 62324Propionyl chlorideHCID 6451240Aluminum(III) Chloride2×

Product 1

HCID 13368787p-N,N-dimethylaminoethylpropiophenoneYield 81.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6348Carbon DisulfideSolvent

Procedure

Anhydrous aluminium chloride (66 g) was added to a solution of N,N-dimethylphenethylamine (22.358 g) in dried carbon disulfide (225 ml). Then, propionyl chloride (15.27 g) was added dropwise to the solution at 50° to 60° C. with stirring over a period of about 1 hour and the solution was refluxed with stirring for 4.5 hours. Cold water was added to the solution to decompose the aluminium chloride. The solution was adjusted to weak alkaline with sodium hydroxide solution and extracted with ethyl ether. The ethereal extract was dried over anhydrous sodium sulfate, concentrated and distilled under reduced pressure to give p-N,N-dimethylaminoethylpropiophenone (25 g, 81%) as a fraction boiling at 115°-117° C./1-2 mmHg.

Workup

  1. temperaturethe solution was refluxed
  2. stirringwith stirring for 4.5 hours
  3. extractionextracted with ethyl ether
  4. extractionThe ethereal extract
  5. dry with materialwas dried over anhydrous sodium sulfate
  6. concentrationconcentrated
  7. distillationdistilled under reduced pressure

Sources & evidence

ORD record
ord-d24e2daa5c394157b6a32ab7db161b82
Source dataset
uspto-grants-1985_04
Patent number
US04511550

Reaction notes

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