1-(2-Methoxyphenyl)piperazine → HCID 15542631, compound

HRID 276898Notes

Reaction equation

HRID 276898 reaction equation
Br[CH2:2][CH2:3][C:4]12[CH2:15][CH2:14][CH2:13][C:11]3[C:12]1=[C:7]([CH:8]=[CH:9][CH:10]=3)[NH:6][C:5]2=[O:16].[CH3:17][O:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[N:25]1[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]1.C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>CN(C)C=O.O>[CH3:17][O:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[N:25]1[CH2:30][CH2:29][N:28]([CH2:2][CH2:3][C:4]23[CH2:15][CH2:14][CH2:13][C:11]4[C:12]2=[C:7]([CH:8]=[CH:9][CH:10]=4)[NH:6][C:5]3=[O:16])[CH2:27][CH2:26]1

Participants

7

Reactant 4

HCID 13461-(2-Methoxyphenyl)piperazineHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 15542638HCID 15542638, compound

Product 1

HCID 15542631HCID 15542631, compoundYield 32.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

2a-(2-Bromoethyl)-2a,3,4,5-tetrahydrobenz[cd]indole-2(1H)-one (140 mg, 0.5 mmol), 4-(2-methoxyphenyl)piperazine (148 mg, 0.77 mmol) and potassium carbonate (138 mg, 1 mmol) were stirred in anhydrous N,N-dimethylformamide (5 ml) at room temperature for 2 hours. The reaction solution was mixed with ethyl acetate (50 ml) and water (50 ml). The ethyl acetate layer was washed with water and dried with anhydrous sodium sulfate. Then the compound obtained by the evaporation of the solvent under a reduced pressure was separated and purified by a silica gel column chromatography to obtain 63 mg of the title compound (32% in yield).

Workup

  1. washThe ethyl acetate layer was washed with water
  2. dry with materialdried with anhydrous sodium sulfate
  3. customThen the compound obtained by the evaporation of the solvent under a reduced pressure
  4. customwas separated
  5. custompurified by a silica gel column chromatography

Sources & evidence

ORD record
ord-64049740a4084836a366dc324a1634db
Source dataset
uspto-grants-2002_03
Patent number
US06355642B1

Reaction notes

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