HCID 18377422, compound → HCID 16748803, compound

HRID 2301150Notes

Reaction equation

HRID 2301150 reaction equation
C([N:8]1[CH2:13][CH2:12][N:11]([C:14]([CH3:22])([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH3:15])[CH2:10][CH2:9]1)C1C=CC=CC=1.[H][H]>C(O)C.[C].[Pd]>[CH3:22][C:14]([N:11]1[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]1)([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH3:15]

Participants

5

Reactant 2

HCID 18377422HCID 18377422, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 16748803HCID 16748803, compound

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

1-Benzyl-4-(1-methyl-1-phenyl-ethyl)-piperazine (290 mg, 1.0 mmol) was dissolved in ethanol (3 ml), and the solution was mixed with 10% palladium-carbon (60 mg) and stirred at room temperature for 15 hours in an atmosphere of hydrogen. The catalyst was removed by filtering the reaction solution, and the solvent was removed by evaporation under a reduced pressure to obtain crude 4-(1-methyl-1-phenyl-ethyl)-piperazine. The thus obtained crude 4-(1-methyl-1-phenyl-ethyl)-piperazine, 2a-(4-bromobutyl)-2a,3,4,5-tetrahydro-1H-benz[cd]indol-2-one (310 mg, 1.0 mmol) and potassium carbonate (210 mg, 1.5 mmol) were stirred at room temperature for 14 hours in anhydrous N,N-dimethylformamide (3 ml). The reaction solution was mixed with ethyl acetate and washed with water and saturated brine, the solvent was removed by evaporation under a reduced pressure and then the thus obtained residue was dissolved in dichloromethane. The dichloromethane solution was washed with water and saturated brine and dried with anhydrous sodium sulfate. The solvent was removed by evaporation from the organic layer under a reduced pressure and the thus obtained material was separated and purified by a silica gel column chromatography to obtain 33 mg (0.076 mmol, 7.7% in yield) of the title compound.

Workup

  1. customThe catalyst was removed
  2. filtrationby filtering the reaction solution
  3. customthe solvent was removed by evaporation under a reduced pressure

Sources & evidence

ORD record
ord-25e78a1b52b44e978b8e434ec2c35689
Source dataset
uspto-grants-2002_12
Patent number
US06498251B1

Reaction notes

Loading…