Potassium Carbonate → 2a-[4-{4-(4-Chlorophenyl)-4-hydroxy-piperidyl}butyl]-2a,3,4,5-tetrahydrobenz[cd]indole-2(1H)-one

HRID 276899Notes

Reaction equation

HRID 276899 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][C:6]12[CH2:17][CH2:16][CH2:15][C:13]3[C:14]1=[C:9]([CH:10]=[CH:11][CH:12]=3)[NH:8][C:7]2=[O:18].[Cl:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]2([OH:32])[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]2)=[CH:22][CH:21]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[Cl:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]2([OH:32])[CH2:27][CH2:28][N:29]([CH2:2][CH2:3][CH2:4][CH2:5][C:6]34[CH2:17][CH2:16][CH2:15][C:13]5[C:14]3=[C:9]([CH:10]=[CH:11][CH:12]=5)[NH:8][C:7]4=[O:18])[CH2:30][CH2:31]2)=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 382824-(4-Chlorophenyl)-4-hydroxypiperidineHCID 105908942a-(4-Bromobutyl)-2a,3,4,5-tetrahydrobenz[cd]indole-2(1H)-one

Product 1

HCID 155426322a-[4-{4-(4-Chlorophenyl)-4-hydroxy-piperidyl}butyl]-2a,3,4,5-tetrahydrobenz[cd]indole-2(1H)-oneYield 90%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2a-(4-bromobutyl)-2a,3,4,5-tetrahydrobenz[cd]indole-2(1H)-one (390 mg, 1.3 mmol), 4-(4-chlorophenyl) -4-hydroxypiperidine (290 mg, 1.4 mmol) and potassium carbonate (260 mg, 1.9 mmol) were stirred in anhydrous N,N-dimethylformamide (10 ml) at 60° C. for 3 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 490 mg of the title compound (1.1 mmol, 90% in yield).

Workup

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

Sources & evidence

ORD record
ord-fd00eab69ab34a328a50c3e16fe93e0e
Source dataset
uspto-grants-2002_03
Patent number
US06355642B1

Reaction notes

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