Triethylamine → HCID 13649190, compound

HRID 648976Notes

Reaction equation

HRID 648976 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][C:8](=[O:13])[CH2:7]2)([OH:3])=O.C(N(CC)CC)C.ClC(OCC(C)C)=O.[CH2:29]([N:36]1[CH2:41][CH2:40][NH:39][CH2:38][CH2:37]1)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>CN(C=O)C>[CH2:29]([N:36]1[CH2:41][CH2:40][N:39]([C:1]([C:4]2[CH:5]=[C:6]3[C:10](=[CH:11][CH:12]=2)[NH:9][C:8](=[O:13])[CH2:7]3)=[O:3])[CH2:38][CH2:37]1)[C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 62365Isobutyl chloroformateHCID 759941-BenzylpiperazineHCID 27733182-Oxindole-5-carboxylic acid

Product 1

HCID 13649190HCID 13649190, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 0.88 g of 5-carboxyoxindol in 10 ml of DMF was added under ice-cooling 0.82 ml of triethylamine, and 0.77 ml of isobutyl chloroformate was added thereto subsequently. The mixture was stirred at the same temperature for 1 hour. Then, 1.1 g of 1-benzylpiperazine was added thereto, and the mixture was stirred at room temperature overnight. After the reaction was completed, DMF was removed under reduced pressure, and to the residue was added an aqueous sodium hydrogencarbonate solution and extracted with chloroform. After washing with water and drying over magnesium sulfate, chloroform was distilled off under reduced pressure. The resultant residue was purified by silica-gel column chromatography (eluent: methylene chloride:methanol=50:1) and recrystallized from isopropyl alcohol to give 0.7 g of 5-(4-benzyl-1-piperazinylcarbonyl)oxindol.

Workup

  1. additionwas added
  2. stirringthe mixture was stirred at room temperature overnight
  3. customDMF was removed under reduced pressure
  4. additionto the residue was added an aqueous sodium hydrogencarbonate solution
  5. extractionextracted with chloroform
  6. washAfter washing with water
  7. dry with materialdrying over magnesium sulfate, chloroform
  8. distillationwas distilled off under reduced pressure
  9. customThe resultant residue was purified by silica-gel column chromatography (eluent: methylene chloride:methanol=50:1)
  10. customrecrystallized from isopropyl alcohol

Sources & evidence

ORD record
ord-a37b526dc547484abf65a3d94b5d4500
Source dataset
uspto-grants-1988_04
Patent number
US04737501

Reaction notes

Loading…