1,2,3,4-Tetrahydroisoquinoline → 2a-(4-(1,2,3,4-Tetrahydroisoquinolin-2-yl)butyl)-1-methyl-2a,3,4,5-tetrahydro-1H-benz[cd]indol-2-one

HRID 2301107Notes

Reaction equation

HRID 2301107 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)[N:8]([CH3:18])[C:7]2=[O:19].[CH2:20]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH2:23][CH2:22][NH:21]1.C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>CN(C)C=O>[CH2:20]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH2:23][CH2:22][N:21]1[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)[N:8]([CH3:18])[C:7]2=[O:19]

Participants

6

Reactant 4

HCID 70461,2,3,4-TetrahydroisoquinolineHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 110563612a-(4-Bromobutyl)-1-methyl-2a,3,4,5-tetrahydro-1H-benz[cd]indol-2-one

Product 1

HCID 99515012a-(4-(1,2,3,4-Tetrahydroisoquinolin-2-yl)butyl)-1-methyl-2a,3,4,5-tetrahydro-1H-benz[cd]indol-2-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2a-(4-Bromobutyl)-1-methyl-2a,3,4,5-tetrahydro-1H-benz[cd]indol-2-one (120 mg, 0.37 mmol), 1,2,3,4-tetrahydroisoquinoline (55 mg, 0.41 mmol) and potassium carbonate (77 mg, 0.56 mmol) were stirred at room temperature for 18 hours in anhydrous N,N-dimethylformamide (1 ml). The reaction solution was mixed with ethyl acetate, washed with water and saturated brine and dried with anhydrous magnesium 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 130 mg (0.34 mmol, 90% in yield) of the title compound.

Workup

  1. washwashed with water and saturated brine
  2. dry with materialdried with anhydrous magnesium sulfate
  3. customthe solvent was removed by evaporation under a reduced pressure
  4. customthe thus obtained material was separated
  5. custompurified by a silica gel column chromatography
  6. customto obtain

Sources & evidence

ORD record
ord-3f48a005b8a24806b157ec5da3262246
Source dataset
uspto-grants-2002_12
Patent number
US06498251B1

Reaction notes

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