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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2301107Generated: November 2, 2026

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

https://huagongshe.com/reaction/2301107

Reaction equation

Participants

RoleNameHCIDCharge
Reactant1,2,3,4-TetrahydroisoquinolineHCID 7046—
ReactantEthyl AcetateHCID 8857—
ReactantPotassium CarbonateHCID 11430—
Reactant2a-(4-Bromobutyl)-1-methyl-2a,3,4,5-tetrahydro-1H-benz[cd]indol-2-oneHCID 11056361—
SolventDimethylformamideHCID 6228—
Product2a-(4-(1,2,3,4-Tetrahydroisoquinolin-2-yl)butyl)-1-methyl-2a,3,4,5-tetrahydro-1H-benz[cd]indol-2-oneHCID 9951501—

Reaction Steps

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.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS06498251B1
Source datasetuspto-grants-2002_12
ORD IDord-3f48a005b8a24806b157ec5da3262246
Source noteuspto-grants-2002_12