Water → HCID 14257911, compound

HRID 231595Notes

Reaction equation

HRID 231595 reaction equation
[CH3:1][N:2]([CH3:12])[C:3](=[O:11])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[CH3:13][N:14]([CH3:18])[CH2:15][CH2:16]Cl.O>C1(C)C=CC=CC=1>[CH3:12][N:2]([CH3:1])[C:3](=[O:11])[CH:4]([C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1)[CH2:16][CH2:15][N:14]([CH3:18])[CH3:13]

Participants

5

Reactant 3

HCID 962WaterHCID 79012-Chloro-N,N-dimethylethylamineHCID 87853Acetamide, N,N-dimethyl-2-phenyl- (8CI)

Product 1

HCID 14257911HCID 14257911, compoundYield 76.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent4×

Procedure

To a mechanically-stirred, refluxing suspension of 5.85 g (0.15 mol) of NaNH2 in 150 ml of toluene, was added dropwise under N2, 50 ml of a toluene solution consisting of 16.3 g (0.1 mol) of N,N-dimethyl-phenylacetamide (prepared by reaction of phenylacetyl chloride and N,N-dimethylamine in CH2Cl2 solvent) in toluene, and the mixture was stirred at reflux for 4 hr. Then, 16.5g (0.15 mol) of 2-(dimethylamino)ethyl chloride in 100 ml of toluene was added dropwise. The mixture was refluxed for 6 hr and then stirred at RT for 16 hr. Water (150 ml) was added to the mixture, and then the organic layer was separated and extracted with 1N HCl. The acid extract was basified in the cold with 2.5N NaOH and the basic solution extracted with Et2O. The ether extract was dried (Na2SO4), concentrated, and distilled to afford 18 g (76.8%) of N,N-dimethyl-4-dimethylamino-2-phenylbutanamide as a colorless oil, bp 108°-110°/0.2 mm.

Workup

  1. temperatureTo a mechanically-stirred, refluxing
  2. additionwas added dropwise under N2
  3. temperatureat reflux for 4 hr
  4. temperatureThe mixture was refluxed for 6 hr
  5. stirringstirred at RT for 16 hr
  6. customthe organic layer was separated
  7. extractionextracted with 1N HCl
  8. extractionThe acid extract
  9. extractionthe basic solution extracted with Et2O
  10. extractionThe ether extract
  11. dry with materialwas dried (Na2SO4)
  12. concentrationconcentrated
  13. distillationdistilled

Sources & evidence

ORD record
ord-d8f3ace94b21430984dd6e71ff647c0d
Source dataset
uspto-grants-1989_07
Patent number
US04847301

Reaction notes

Loading…