Diisopropyl Ether → 2a-(4-Bromobutyl)-1-methyl-2a,3,4,5-tetrahydro-1H-benz[cd]indol-2-one

1-Methyl-2a,3,4,5-tetrahydrobenz[cd]indole-2(1H) -one (3.7 g, 20 mmol) was dissolved in anhydrous N,N-dimethylformamide (50 ml). Thereto was added sodium hydride (60% content, 800 mg, 20 mmol), and the resulting solution was stirred at a room temperature for 30 minutes. The reaction solution was cooled in an ice bath of −10° C., mixed with 1,4-dibromobutane (7.0 ml) and then 1 hour of the reaction was carried out while temperature of the reaction solution was increased to a room temperature. The reaction solution was mixed with diisopropyl ether (150 ml) and water (100 ml), and the reaction product was extracted. Then the resulting organic layer was washed three times with water and dried with anhydrous sodium sulfate. Diisopropyl ether was evaporated under a reduced pressure, and the thus obtained oily residue was separated and purified by a silica gel column chromatography (developing system: diisopropyl ether) to obtain 4.8 g of the title compound (15 mmol, 75% in yield).

1. temperatureThe reaction solution was cooled in an ice bath of −10° C.
2. custom1 hour of the reaction
3. temperaturewas increased to a room temperature
4. extractionthe reaction product was extracted
5. washThen the resulting organic layer was washed three times with water
6. dry with materialdried with anhydrous sodium sulfate
7. customDiisopropyl ether was evaporated under a reduced pressure
8. customthe thus obtained oily residue was separated
9. custompurified by a silica gel column chromatography (developing system: diisopropyl ether)

ORD record

ord-d876a2c52e08489884956b0b6b1c5428

Source dataset

uspto-grants-2002_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06355642B1