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

HRID 276880

Reaction equation

HRID 276880 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)-oneYield 34.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2a, 3,4,5-Tetrahydrobenz [cd]indole-2(1H) -one (3.0 g, 17 mmol) was dissolved in anhydrous N,N-dimethylformamide (120 ml). Thereto was added an oily sodium hydride (760 mg, 19 mmol), and the resulting solution was stirred at a 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 evaporated under a reduced pressure, and the thus obtained residue was mixed with ethyl acetate, water and hydrochloric acid (1 N). The reaction product was extracted with ethyl acetate, washed with saturated brine and dried with anhydrous sodium sulfate. Then the compound obtained by the evaporation of the solvent under a reduced pressure was separated and purified by a silica gel column chromatography to obtain 1.8 g of the title compound (5.8 mmol, 33% in yield).

Workup

  1. stirringagain stirred for 17 hours
  2. customThe solvent was evaporated under a reduced pressure
  3. additionthe thus obtained residue was mixed with ethyl acetate, water and hydrochloric acid (1 N)
  4. extractionThe reaction product was extracted with ethyl acetate
  5. washwashed with saturated brine
  6. dry with materialdried with anhydrous sodium sulfate
  7. customThen the compound obtained by the evaporation of the solvent under a reduced pressure
  8. customwas separated
  9. custompurified by a silica gel column chromatography

Sources & evidence

ORD record
ord-47990322cb844c318103aa69840dda39
Source dataset
uspto-grants-2002_03
Patent number
US06355642B1

Linked notes

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