Hydrochloric Acid → HCID 15233446, compound

HRID 1440227Notes

Reaction equation

HRID 1440227 reaction equation
[CH3:1][N:2]([CH3:20])[CH2:3][CH2:4][CH:5]([C:8]1[CH:13]=[C:12]([O:14][CH3:15])[C:11]([O:16][CH3:17])=[C:10]([O:18][CH3:19])[CH:9]=1)[C:6]#[N:7].[OH-].[K+].C(OCC)(=[O:25])C.Cl>CC(O)(C)C>[CH3:20][N:2]([CH3:1])[CH2:3][CH2:4][CH:5]([C:8]1[CH:9]=[C:10]([O:18][CH3:19])[C:11]([O:16][CH3:17])=[C:12]([O:14][CH3:15])[CH:13]=1)[C:6]([NH2:7])=[O:25]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 14797Potassium HydroxideHCID 15233445HCID 15233445, compound

Product 1

HCID 15233446HCID 15233446, compound

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

In 8 ml of 2-methyl-2-propanol was dissolved 0.84 g of 4-dimethylamino-2-(3,4,5-trimethoxyphenyl)butyronitrile, followed by addition of 1.0 g of ground potassium hydroxide. The mixture was refluxed for 1 hour. After cooling the reaction mixture, the insoluble matters were filtered off and the filtrate was concentrated under reduced pressure. To the residue thus obtained were added ethyl acetate and 10% hydrochloric acid. The aqueous layer was separated and made strongly basic with sodium hydroxide for salting-out and the basic substance was extracted with ethyl acetate. The ethyl acetate layer was washed with a mixture of water and saturated aqueous sodium chloride (1:1) and a saturated aqueous solution of sodium chloride in turn, then dried over anhydrous sodium sulfate and concentrated to dryness under reduced pressure. The crystalline residue thus obtained (0.59 g) was recrystallized from ethyl acetate to provide 0.35 g of 4-dimethylamino-2-(3,4,5-trimethoxyphenyl)butyramide.

Workup

  1. temperatureThe mixture was refluxed for 1 hour
  2. temperatureAfter cooling the reaction mixture
  3. filtrationthe insoluble matters were filtered off
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customTo the residue thus obtained
  6. customThe aqueous layer was separated
  7. extractionthe basic substance was extracted with ethyl acetate
  8. washThe ethyl acetate layer was washed with a mixture of water and saturated aqueous sodium chloride (1:1)
  9. dry with materiala saturated aqueous solution of sodium chloride in turn, then dried over anhydrous sodium sulfate
  10. concentrationconcentrated to dryness under reduced pressure
  11. customThe crystalline residue thus obtained (0.59 g)
  12. customwas recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-439e9ba567e1428c9832e473b708456d
Source dataset
uspto-grants-1996_03
Patent number
US05498635

Reaction notes

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