Water → 5-(4-Benzyl-1-piperazinyl)oxindol

HRID 648974Notes

Reaction equation

HRID 648974 reaction equation
Br.[N:2]1([C:8]2[CH:9]=[C:10]3[C:14](=[CH:15][CH:16]=2)[NH:13][C:12](=[O:17])[CH2:11]3)[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.[CH2:18](Cl)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C(N(CC)CC)C.O>C(#N)C>[CH2:18]([N:5]1[CH2:6][CH2:7][N:2]([C:8]2[CH:9]=[C:10]3[C:14](=[CH:15][CH:16]=2)[NH:13][C:12](=[O:17])[CH2:11]3)[CH2:3][CH2:4]1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7503Benzyl ChlorideHCID 8471TriethylamineHCID 136460315-(1-Piperazinyl)oxindol.hydrobromide

Product 1

HCID 136460375-(4-Benzyl-1-piperazinyl)oxindolYield 67.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 5-(1-piperazinyl)oxindol.hydrobromide (1.0 g), 1.2 g of benzyl chloride and 1.1 g of triethylamine in 20 ml of acetonitrile was stirred at room temperature for 6 hours. The reaction mixture was poured into a large amount of water and extracted with chloroform. After washing with water, the extract was dried over anhydrous sodium sulfate and chloroform was removed. The residue was recrystallized from isopropyl alcohol to give 0.7 g of 5-(4-benzyl-1-piperazinyl)oxindol.

Workup

  1. extractionextracted with chloroform
  2. washAfter washing with water
  3. dry with materialthe extract was dried over anhydrous sodium sulfate and chloroform
  4. customwas removed
  5. customThe residue was recrystallized from isopropyl alcohol

Sources & evidence

ORD record
ord-fb9c92dfdff14f48a29c27b2f62774cd
Source dataset
uspto-grants-1988_04
Patent number
US04737501

Reaction notes

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