Oxindole → 3-[2-(4-Methylpiperazin-1-yl)-benzylidene]-1,3-dihydro-indol-2-one

HRID 583811Notes

Reaction equation

HRID 583811 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:15]=[CH:14][CH:13]=[CH:12][C:9]=2[CH:10]=O)[CH2:4][CH2:3]1.[NH:16]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH2:18][C:17]1=[O:25]>C(O)C>[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:15]=[CH:14][CH:13]=[CH:12][C:9]=2[CH:10]=[C:18]2[C:19]3[C:24](=[CH:23][CH:22]=[CH:21][CH:20]=3)[NH:16][C:17]2=[O:25])[CH2:4][CH2:3]1

Participants

4

Reactant 2

HCID 321710OxindoleHCID 27955662-(4-Methylpiperazin-1-yl)benzaldehyde

Product 1

HCID 27414603-[2-(4-Methylpiperazin-1-yl)-benzylidene]-1,3-dihydro-indol-2-oneYield 116.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Under nitrogen in a dry round bottom flask fitted with a condensor and magnetic stir bar were placed 2-(4methyl-1-piperazinyl)-benzaldehyde (0.152 g, 0.75 g, 0.75 mmol), oxindole (0.104 g, 0.78 mmol) pyrrolidine (62 μL) and ethanol (7.0 mL). The mixture was heated to reflux for 16 hours, cooled and evaporated under reduced pressure. The residue was partitioned between ethyl acetate and water and the organic layer was washed with saturated aqueous sodium chloride (NaCl), dried over magnesium sulfate (MgSO4)1, filtered and absorbed onto 437 mg of silica gel. Elution with ethyl acetate (EtOAc) (125 mL), 1% methanol (CH3OH) in EtOAc (100 mL), 2% CH3OH in EtOAc (100 mL) and 4% CH3OH+1% triethylamine (Et3N) In EtOAc (50 mL) gave 280 mg of a yellow solid. Recrystallization from hot CH3OH gave the title product, m.p. 226-2280° C.

Workup

  1. customUnder nitrogen in a dry round bottom flask fitted with a condensor and magnetic stir bar
  2. temperatureThe mixture was heated
  3. temperatureto reflux for 16 hours
  4. temperaturecooled
  5. customevaporated under reduced pressure
  6. customThe residue was partitioned between ethyl acetate and water
  7. washthe organic layer was washed with saturated aqueous sodium chloride (NaCl)
  8. dry with materialdried over magnesium sulfate (MgSO4)1
  9. filtrationfiltered
  10. customabsorbed onto 437 mg of silica gel
  11. washElution with ethyl acetate (EtOAc) (125 mL), 1% methanol (CH3OH) in EtOAc (100 mL), 2% CH3OH in EtOAc (100 mL)

Sources & evidence

ORD record
ord-efafad518fe74e419bf48d8d2b91b81c
Source dataset
uspto-grants-2005_08
Patent number
US06924289B2

Reaction notes

Loading…