Pyridine → HCID 13649190, compound

HRID 648981Notes

Reaction equation

HRID 648981 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.N1C=CC=CC=1.S(Cl)(Cl)=O.[CH2:24]([N:31]1[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>C(Cl)Cl>[CH2:24]([N:31]1[CH2:36][CH2:35][N:34]([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])[CH2:33][CH2:32]1)[C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 24386Thionyl ChlorideHCID 759941-BenzylpiperazineHCID 27733182-Oxindole-5-carboxylic acid

Product 1

HCID 13649190HCID 13649190, compoundYield 9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a suspension of 1.76 g of 5-carboxyoxindol in 200 ml of methylene chloride was added 2 ml of pyridine. After completion of addition, to the suspension was added dropwise 1.4 g of thionyl chloride with stirring held at 0° to 20° C. After completion of addition, the mixture was stirred at the same temperature for 1 hour, and a solution of 1.74 g of benzylpiperazine in 10 ml of methylene chloride was added dropwise thereto. The mixture was then stirred for 4 hours at room temperature. The reaction mixture was thoroughly washed with an aqueous potassium carbonate solution, then washed with water, and dilute hydrochloric acid, dried over sodium sulfate, and the solvent was distilled off. The residue was isolated and purified by silica-gel column chromatography [silica-gel: WAKO C-200, eluent: chloroform:methanol (V/V)=20:1] followed by recrystallization from isopropyl alcohol to give 298 mg of 5-(4-benzyl-1-piperazinylcarbonyl)oxindol.

Workup

  1. additionAfter completion of addition
  2. customheld at 0° to 20° C
  3. additionAfter completion of addition
  4. stirringthe mixture was stirred at the same temperature for 1 hour
  5. stirringThe mixture was then stirred for 4 hours at room temperature
  6. washThe reaction mixture was thoroughly washed with an aqueous potassium carbonate solution
  7. washwashed with water, and dilute hydrochloric acid
  8. dry with materialdried over sodium sulfate
  9. distillationthe solvent was distilled off
  10. customThe residue was isolated
  11. custompurified by silica-gel column chromatography [silica-gel: WAKO C-200, eluent: chloroform:methanol (V/V)=20:1]
  12. customfollowed by recrystallization from isopropyl alcohol

Sources & evidence

ORD record
ord-00651fbc754948d5b30720fd11d39c6e
Source dataset
uspto-grants-1988_04
Patent number
US04737501

Reaction notes

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