1-Bromo-2-methylpropane → HCID 13649199, compound

HRID 648977Notes

Reaction equation

HRID 648977 reaction equation
[ClH:1].[N:2]1([C:8]([C:10]2[CH:11]=[C:12]3[C:16](=[CH:17][CH:18]=2)[NH:15][C:14](=[O:19])[CH2:13]3)=[O:9])[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.C1CCN2C(=NCCC2)CC1.[CH2:31](Br)[CH:32]([CH3:34])[CH3:33].C(=O)([O-])O.[Na+]>C(#N)C.C(N(CC)CC)C>[ClH:1].[CH2:31]([N:5]1[CH2:6][CH2:7][N:2]([C:8]([C:10]2[CH:11]=[C:12]3[C:16](=[CH:17][CH:18]=2)[NH:15][C:14](=[O:19])[CH2:13]3)=[O:9])[CH2:3][CH2:4]1)[CH:32]([CH3:34])[CH3:33]

Participants

7

Reactant 4

HCID 65551-Bromo-2-methylpropane2×HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 516892Sodium BicarbonateHCID 13649192HCID 13649192, compound

Product 1

HCID 13649199HCID 13649199, compoundYield 32.5%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8471TriethylamineSolvent

Procedure

5-(1-Piperazinylcarbonyl)oxindol hydrochloride (1.0 g), 1.2 g of DBU, and 0.73 g of isobutyl bromide were suspended in 15 ml of acetonitrile and the suspension was reflexed for 6 hours. To the mixture were then added 0.6 ml of triethylamine and 0.73 g of isobutyl bromide and the mixture was further reflexed for 8 hours. The reaction mixture was poured into a saturated aqueous solution of sodium hydrogencarbonate and extracted with chloroform. The chloroform layer was washed with a saturated saline solution and dried over sodium sulfate. The residue obtained after the solvent was distilled off was purified by silica-gel column chromatography (eluent: dichloromethane:methanol=20:1). The product was converted into the hydrochloride with acetone and hydrochloricacid, and recrystallized from a mixture of ethanol and methanol to give 0.39 g of 5-(4-isobutyl-1-piperazinylcarbonyl)oxindol hydrochloride.

Workup

  1. waitthe mixture was further reflexed for 8 hours
  2. extractionextracted with chloroform
  3. washThe chloroform layer was washed with a saturated saline solution
  4. dry with materialdried over sodium sulfate
  5. customThe residue obtained after the solvent
  6. distillationwas distilled off
  7. customwas purified by silica-gel column chromatography (eluent: dichloromethane:methanol=20:1)
  8. customrecrystallized from a mixture of ethanol and methanol

Sources & evidence

ORD record
ord-dc1fbef8014e4758991aea2bebd39d34
Source dataset
uspto-grants-1988_04
Patent number
US04737501

Reaction notes

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