Acetic Acid → 5,6-Dimethoxy-3[4(2-methylpropyloxycarbonyl)piperazino]methylene oxindole

HRID 47071

Reaction equation

HRID 47071 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][C:11]=1[O:12][CH3:13])[NH:8][C:7](=[O:14])[C:6]2=[CH:15]O.C(O)(=O)C.[CH2:21]([O:25][C:26]([N:28]1[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]1)=[O:27])[CH:22]([CH3:24])[CH3:23]>C1C=CC=CC=1.O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][C:11]=1[O:12][CH3:13])[NH:8][C:7](=[O:14])[C:6]2=[CH:15][N:31]1[CH2:30][CH2:29][N:28]([C:26]([O:25][CH2:21][CH:22]([CH3:24])[CH3:23])=[O:27])[CH2:33][CH2:32]1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 11788701Isobutyl piperazine-1-carboxylateHCID 178486553HCID 178486553, compound

Product 1

HCID 539513465,6-Dimethoxy-3[4(2-methylpropyloxycarbonyl)piperazino]methylene oxindole

Reagents, catalysts & solvents 2

HCID 241BenzeneSolvent2×HCID 962WaterSolvent

Procedure

5.00 g. of 5,6-Dimethoxy-3-hydroxymethylene oxindole, 2.5 g. acetic acid and 6.5 g. piperazine-N-carboxylic acid isobutyl ester (U.S. Pat. No. 3,635,979) in 40 ml. benzene was refluxed using a water separator to remove the water as it formed. After 20 minutes, 200 ml. benzene was added and the solution extracted with potassium carbonate and water. The benzene solution was treated with magnesium sulfate and charcoal, filtered, concentrated and the residue crystallized from isopropyl alcohol and ether to give 5.50 g. product, m.p. 195°-197° C.

Workup

  1. customto remove the water as it
  2. customformed
  3. extractionthe solution extracted with potassium carbonate and water
  4. additionThe benzene solution was treated with magnesium sulfate and charcoal
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customthe residue crystallized from isopropyl alcohol and ether
  8. customto give 5.50 g

Sources & evidence

ORD record
ord-72970bca4ce742a8bdfe7b556c92414c
Source dataset
uspto-grants-1979_11
Patent number
US04176191

Linked notes

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