Piperazine → HCID 18001227, compound

HRID 478198Notes

Reaction equation

HRID 478198 reaction equation
Br[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]([S:11]([C:14]2[CH:20]=[CH:19][C:17]([CH3:18])=[CH:16][CH:15]=2)(=[O:13])=[O:12])[CH:3]=1.[NH:21]1[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]1.C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+]>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[N:21]1([C:2]2[C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[N:4]([S:11]([C:14]3[CH:20]=[CH:19][C:17]([CH3:18])=[CH:16][CH:15]=3)(=[O:13])=[O:12])[CH:3]=2)[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]1

Participants

7

Reactant 4

HCID 4837PiperazineHCID 10796Cesium carbonateHCID 634876Binap, (A+-)-HCID 112102743-Bromo-1-(P-toluenesulfonyl)indole

Product 1

HCID 18001227HCID 18001227, compoundYield 65%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolvent

Procedure

To a solution of 3-bromo-1-tosylindole (105 mg, 0.3 mmol) and anhydrous piperazine (258 mg, 3.0 mmol) in toluene (4.5 mL) was added palladium acetate (13.4 mg, 0.055 mmol), BINAP (40.3 mg, 0.065 mmol), and cesium carbonate (318 mmol, 0.9 mmol), and the resulting mixture was refluxed for 6 hours. The reaction solution was cooled to room temperature and the precipitated salt was separated by filtration, and the filtrate was concentrated to afford a crude product. The crude product was purified by column chromatography on a silica gel (eluent; ammonia-saturated chloroform) to afford the title compound (69 mg, yield: 65%) as a colorless viscous oil.

Workup

  1. temperaturethe resulting mixture was refluxed for 6 hours
  2. customthe precipitated salt was separated by filtration
  3. concentrationthe filtrate was concentrated
  4. customto afford a crude product
  5. customThe crude product was purified by column chromatography on a silica gel (eluent; ammonia-saturated chloroform)

Sources & evidence

ORD record
ord-646944f7014c479d831f660f8011add5
Source dataset
uspto-grants-2003_11
Patent number
US06642228B1

Reaction notes

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