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

HRID 276882Notes

Reaction equation

HRID 276882 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][CH2:21]Br>CN(C)C=O>[Br:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][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 81001,5-DibromopentaneHCID 24758Sodium hydrideHCID 5993752a,3,4,5-Tetrahydrobenzo[cd]indol-2(1H)-one

Product 1

HCID 155426342a-(5-Bromopentyl)-2a, 3,4,5-tetrahydrobenz[cd]indole-2(1H)-oneYield 12.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2a, 3,4,5-Tetrahydrobenz [cd]indole-2(1H) -one (1.0 g, 5.8 mmol) was dissolved in anhydrous N,N-dimethylformamide (40 ml). Thereto was added sodium hydride (250 mg, 6.3 mmol), and the resulting solution was stirred at a room temperature for 1 hour. The reaction solution was mixed with 1,5-dibromopentane (2.4 ml, 17 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 and water. 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 230 mg of the title compound (0.70 mmol, 12% 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 and water
  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-f44dc5d8d2e24651943c6afd281e9c0f
Source dataset
uspto-grants-2002_03
Patent number
US06355642B1

Reaction notes

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