1-(2-Methoxyphenyl)piperazine → HCID 15489020, compound

HRID 2187041Notes

Reaction equation

HRID 2187041 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][C@@:6]12[CH2:17][CH2:16][CH2:15][C:13]3[C:14]1=[C:9]([CH:10]=[CH:11][CH:12]=3)[NH:8][C:7]2=[O:18].[CH3:19][O:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[N:27]1[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]1.C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>CN(C)C=O>[CH3:19][O:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[N:27]1[CH2:32][CH2:31][N:30]([CH2:2][CH2:3][CH2:4][CH2:5][C@@:6]23[CH2:17][CH2:16][CH2:15][C:13]4[C:14]2=[C:9]([CH:10]=[CH:11][CH:12]=4)[NH:8][C:7]3=[O:18])[CH2:29][CH2:28]1

Participants

6

Reactant 4

HCID 13461-(2-Methoxyphenyl)piperazineHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 15887274HCID 15887274, compound

Product 1

HCID 15489020HCID 15489020, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(S)-2a-(4-bromobutyl)-2a,3,4,5-tetrahydro-1H-benz[cd]indol-2-one (308 mg, 1.0 mmol), 4-(2-methoxyphenyl)piperazine (415 mg, 2.1 mmol) and potassium carbonate (280 mg, 2.0 mmol) in anhydrous N,N-dimethylformamide (10 ml) were stirred at room temperature for 18 hours. Then, ethyl acetate (80 ml) was added to the resulting reaction mixture, which was washed with water and saturated saline solution, successively dried over anhydrous sodium sulfate, followed by evaporating the solvent under reduced pressure. The resulting product was separated and purified by means of silica gel column chromatography, whereby 350 mg (yield 84%) of the above-described object compound could be obtained.

Workup

  1. washwas washed with water and saturated saline solution
  2. dry with materialsuccessively dried over anhydrous sodium sulfate
  3. customby evaporating the solvent under reduced pressure
  4. customThe resulting product was separated

Sources & evidence

ORD record
ord-bd104bbd33dc421ba0ec0c5ac5a3c574
Source dataset
uspto-grants-2002_06
Patent number
US06407112B1

Reaction notes

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