1,4-Dibromobutane → 2a-(4-Bromobutyl)-2a,3,4,5-tetrahydrobenz[cd]indole-2(1H)-one

HRID 2301106Notes

Reaction equation

HRID 2301106 reaction equation
[NH:1]1[C:9]2[CH:8]=[CH:7][CH:6]=[C:5]3[CH2:10][CH2:11][CH2:12][CH:3]([C:4]=23)[C:2]1=[O:13].[H-].[Na+].[Br:16][CH2:17][CH2:18][CH2:19][CH2:20]Br>CN(C)C=O>[Br:16][CH2:17][CH2:18][CH2:19][CH2:20][C:3]12[CH2:12][CH2:11][CH2:10][C:5]3[C:4]1=[C:9]([CH:8]=[CH:7][CH:6]=3)[NH:1][C:2]2=[O:13]

Participants

5

Reactant 3

HCID 80561,4-DibromobutaneHCID 24758Sodium hydrideHCID 5993752a,3,4,5-Tetrahydrobenzo[cd]indol-2(1H)-one

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2a,3,4,5-Tetrahydro-1H-benz[cd]indol-2-one (3.0 g, 17 mmol) was dissolved in anhydrous N,N-dimethylformamide (120 ml), and the solution was mixed with sodium hydride (60%, 760 mg, 190 mmol) and stirred at room temperature for 1 hour. The reaction solution was mixed with 1,4-dibromobutane (6.3 ml, 52 mmol) and again stirred for 17 hours. The solvent was removed by evaporation under a reduced pressure, and ethyl acetate, water and hydrochloric acid (1 N) were added to the resulting residue. 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 1.8 g (5.8 mmol, 33% in yield) of the title compound.

Workup

  1. stirringagain stirred for 17 hours
  2. customThe solvent was removed by evaporation under a reduced pressure, and ethyl acetate, water and hydrochloric acid (1 N)
  3. additionwere added to the resulting residue
  4. extractionThe reaction product was extracted with ethyl acetate
  5. washwashed with saturated brine
  6. dry with materialdried with anhydrous sodium sulfate
  7. customthe solvent was removed by evaporation under a reduced pressure
  8. customthe thus obtained material was separated
  9. custompurified by a silica gel column chromatography
  10. customto obtain

Sources & evidence

ORD record
ord-9cfdd4dab6224060a2d6b526e5309c99
Source dataset
uspto-grants-2002_12
Patent number
US06498251B1

Reaction notes

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