Potassium Carbonate → HCID 10834268, compound

HRID 276920Notes

Reaction equation

HRID 276920 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].[N: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+]>CN(C)C=O>[N:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[N:25]1[CH2:26][CH2:27][N:28]([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][CH2:30]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 944591-(2-Pyridyl)piperazineHCID 105908942a-(4-Bromobutyl)-2a,3,4,5-tetrahydrobenz[cd]indole-2(1H)-one

Product 1

HCID 10834268HCID 10834268, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2a-(4-Bromobutyl)-2a,3,4,5-tetrahydrobenz[cd]indole-2(1H)-one (147 mg, 0.48 mmol), 1-(2-pyridyl)piperazine (86 mg, 0.53 mmol) and potassium carbonate (99 mg, 0.72 mmol) were stirred overnight in anhydrous N,N-dimethylformamide (2 ml) at 60° C. 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, the solvent was evaporated under a reduced pressure and then the thus obtained substance was separated and purified by a silica gel column chromatography to obtain 190 mg of the title compound (0.48 mmol, 100% 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. customthe solvent was evaporated under a reduced pressure
  7. customthe thus obtained substance was separated
  8. custompurified by a silica gel column chromatography

Sources & evidence

ORD record
ord-da283ece69fd44869afe65d90f270fe3
Source dataset
uspto-grants-2002_03
Patent number
US06355642B1

Reaction notes

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