Water → HCID 19009074, compound

HRID 1742219Notes

Reaction equation

HRID 1742219 reaction equation
[CH2:1]([NH:5][C:6](=[O:17])[CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[C:11]([OH:16])[CH:10]=1)[CH2:2][CH2:3][CH3:4].Br[CH2:19][CH2:20]Br.O>CN(C)C=O>[CH2:1]([NH:5][C:6](=[O:17])[CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]2[O:15][CH2:19][CH2:20][O:16][C:11]=2[CH:10]=1)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 962WaterHCID 78391,2-DibromoethaneHCID 15132212HCID 15132212, compound

Product 1

HCID 19009074HCID 19009074, compoundYield 37.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1.5 g of N-butyl-3-(3,4- dihydroxyphenyl)propionamide was dissolved in 10 ml of N,N-dimethylformamide and 2.3 g of potassium carbonate anhydride was added to the solution. Then 2.3 g of 1,2-dibromoethane and 100 mg of cupric oxide were added to the solution and the resulting solution was stirred at 130°-140° C. for 4 hours. After cooling, the solution was poured over iced water and extracted with ethyl acetate; the organic layer was isolated, washed with water, dried with sodium sulfate anhydride and the solvent was removed by evaporation under reduced pressure. The residue was purified by chromatography on a silica gel column with a mixed solvent (chloroform:methanol=100:l) and thus 0.62 g of oily N-butyl-3-(1,4-benzodioxane-6-yl)propionamide was obtained.

Workup

  1. temperatureAfter cooling
  2. extractionextracted with ethyl acetate
  3. customthe organic layer was isolated
  4. washwashed with water
  5. dry with materialdried with sodium sulfate anhydride
  6. customthe solvent was removed by evaporation under reduced pressure
  7. customThe residue was purified by chromatography on a silica gel column with a mixed solvent (chloroform:methanol=100:l)

Sources & evidence

ORD record
ord-99e655001a70411c896cfa8669a7ab06
Source dataset
uspto-grants-1994_08
Patent number
US05338745

Reaction notes

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