2-Chloro-N,N-dimethylethylamine → HCID 54328146, compound

HRID 1762496Notes

Reaction equation

HRID 1762496 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH:15]=[C:16]([C:19]([CH3:22])([CH3:21])[CH3:20])[C:17]=1[OH:18])[CH:8]=[C:9]1[CH2:13][CH2:12][NH:11][C:10]1=[O:14])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[CH3:25][N:26]([CH3:30])[CH2:27][CH2:28]Cl>CN(C)C=O>[CH3:25][N:26]([CH3:30])[CH2:27][CH2:28][N:11]1[CH2:12][CH2:13][C:9](=[CH:8][C:7]2[CH:6]=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[C:17]([OH:18])=[C:16]([C:19]([CH3:22])([CH3:21])[CH3:20])[CH:15]=2)[C:10]1=[O:14]

Participants

5

Reactant 3

HCID 79012-Chloro-N,N-dimethylethylamineHCID 24758Sodium hydrideHCID 538962973-(3,5-Di-tert-butyl-4-hydroxybenzylidene)-2-pyrrolidone

Product 1

HCID 54328146HCID 54328146, compoundYield 48.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

500 mg of 3-(3,5-di-tert-butyl-4-hydroxybenzylidene)-2-pyrrolidone was dissolved in 5 ml of dimethylformamide and 0.2 g of sodium hydride and 0.2 g of 2-dimethylaminoethyl chloride were successively added thereto under ice-cooling. Then the obtained mixture was allowed to react for one hour at room temperature. The reaction mixture was extracted with ethyl acetate, washed with water followed by a saturated saline solution and dried over anhydrous magnesium sulfate. After distilling the ethyl acetate off, the residue was purified by column chromatography with the use of silica gel and benzene/acetone and recrystallized from ethyl acetate/hexane to give 300 mg of the title compound.

Workup

  1. temperatureunder ice-cooling
  2. customto react for one hour at room temperature
  3. extractionThe reaction mixture was extracted with ethyl acetate
  4. washwashed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationAfter distilling the ethyl acetate off, the residue
  7. customwas purified by column chromatography with the use of silica gel and benzene/acetone
  8. customrecrystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-11299e568037424581ca57e6278d052b
Source dataset
uspto-grants-1989_05
Patent number
US04833160

Reaction notes

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