Potassium Carbonate → HCID 18377278, compound

HRID 2301148Notes

Reaction equation

HRID 2301148 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].[CH2:19]([CH:26]1[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH2:19]([CH:26]1[CH2:31][CH2:30][N:29]([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])[CH2:28][CH2:27]1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 317384-BenzylpiperidineHCID 105908942a-(4-Bromobutyl)-2a,3,4,5-tetrahydrobenz[cd]indole-2(1H)-one

Product 1

HCID 18377278HCID 18377278, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2a-(4-Bromobutyl)-2a,3,4,5-tetrahydro-1H-benz[cd]indol-2-one (190 mg, 0.62 mmol), 4-benzyl-piperidine (110 mg, 0.65 mmol) and potassium carbonate (120 mg, 0.88 mmol) were stirred overnight at 60° C. in anhydrous N,N-dimethylformamide (2 ml). The solvent was removed by evaporation under a reduced pressure, and the 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 removed by evaporation under a reduced pressure, and then the thus obtained material was separated and purified by a silica gel column chromatography to obtain 210 mg (1.1 mmol, 85% in yield) of the title compound.

Workup

  1. customThe solvent was removed by evaporation under a reduced pressure
  2. additionthe 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 removed by evaporation under a reduced pressure
  7. customthe thus obtained material was separated
  8. custompurified by a silica gel column chromatography
  9. customto obtain

Sources & evidence

ORD record
ord-3dbb963d54be49e1abb98881887d402c
Source dataset
uspto-grants-2002_12
Patent number
US06498251B1

Reaction notes

Loading…