Water → HCID 10220535, compound

HRID 1742221Notes

Reaction equation

HRID 1742221 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH2:9][CH2:10][C:11]([N:13]2[CH2:17][CH2:16][CH2:15][CH2:14]2)=[O:12])[CH:5]=[CH:6][C:7]=1[OH:8].Br[CH2:19]Br.O>CN(C)C=O>[O:8]1[C:7]2[CH:6]=[CH:5][C:4]([CH2:9][CH2:10][C:11]([N:13]3[CH2:17][CH2:16][CH2:15][CH2:14]3)=[O:12])=[CH:3][C:2]=2[O:1][CH2:19]1

Participants

5

Reactant 3

HCID 962WaterHCID 3024DibromomethaneHCID 14882493HCID 14882493, compound

Product 1

HCID 10220535HCID 10220535, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

0.92 g of N-[3-(3,4-dihydroxyphenyl)-propionylpyrrolidine was dissolved in 10 ml of N,N-dimethylformamide and then 1.2 g of dibromomethane and 1.2 g of potassium carbonate anhydride 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, extracted with ethyl acetate, washed with water and then dried with sodium sulfate anhydride. The solvent was removed by evaporation under reduced pressure and the residue was purified by chromatography on a silica gel column with a mixed solvent (chloroform:methanol=100:l) and thus 0.59 g of oily N-[3-(1.3-benzodioxol-5-yl)propionyl]pyrrolidine was obtained.

Workup

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

Sources & evidence

ORD record
ord-de1074a8e4684c9892c46bee1414a878
Source dataset
uspto-grants-1994_08
Patent number
US05338745

Reaction notes

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