1-(2-Methoxyphenyl)piperazine → 2a-[4-{4-(2-Methoxyphenyl)piperazinyl}butyl]-2a,3,4,5-tetrahydrobenz[cd]indole-2(1H)-one

HRID 276884Notes

Reaction equation

HRID 276884 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+]>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

5

Reactant 3

HCID 13461-(2-Methoxyphenyl)piperazineHCID 11430Potassium CarbonateHCID 105908942a-(4-Bromobutyl)-2a,3,4,5-tetrahydrobenz[cd]indole-2(1H)-one

Product 1

HCID 98450062a-[4-{4-(2-Methoxyphenyl)piperazinyl}butyl]-2a,3,4,5-tetrahydrobenz[cd]indole-2(1H)-oneYield 94.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2a-(4-Bromobutyl)-2a,3,4,5-tetrahydrobenz[cd]indole-2(1H)-one (220 mg, 0.72 mmol), 4-(2-methoxyphenyl)piperazine (150 mg, 0.79 mmol) and potassium carbonate (150 mg, 1.1 mmol) were stirred in anhydrous N,N-dimethylformamide (5 ml) at 50° C. for 4 hours. The solvent was evaporated under a reduced pressure, and the thus obtained residue was mixed with ethyl acetate and water. The reaction product was extracted with ethyl acetate, washed with saturated brine 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 280 mg of the title compound (0.68 mmol, 94% in yield).

Workup

  1. customThe solvent was evaporated under a reduced pressure
  2. additionthe thus obtained residue was mixed with ethyl acetate and water
  3. extractionThe reaction product was extracted with ethyl acetate
  4. washwashed with saturated brine
  5. dry with materialdried with anhydrous sodium sulfate
  6. customThen the compound obtained by the evaporation of the solvent under a reduced pressure
  7. customwas separated
  8. custompurified by a silica gel column chromatography

Sources & evidence

ORD record
ord-05400052ced047f8a15bff83e575e081
Source dataset
uspto-grants-2002_03
Patent number
US06355642B1

Reaction notes

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