Ethyl Acetate → 2a-[4-(4-Methyl-4-phenyl-piperidyl)butyl]-2a,3,4,5-tetrahydrobenz[cd]indole-2(1H)-one

HRID 276904Notes

Reaction equation

HRID 276904 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]([CH3:20])([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)C1C=CC=CC=1.BrC[CH2:23][CH2:24][CH2:25][C:26]12[CH2:37][CH2:36][CH2:35][C:33]3[C:34]1=[C:29]([CH:30]=[CH:31][CH:32]=3)[NH:28][C:27]2=[O:38].C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>C(O)C.[C].[Pd].O>[CH3:20][C:11]1([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:12][CH2:13][N:8]([CH2:1][CH2:23][CH2:24][CH2:25][C:26]23[CH2:37][CH2:36][CH2:35][C:33]4[C:34]2=[C:29]([CH:30]=[CH:31][CH:32]=4)[NH:28][C:27]3=[O:38])[CH2:9][CH2:10]1

Participants

8

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 105908942a-(4-Bromobutyl)-2a,3,4,5-tetrahydrobenz[cd]indole-2(1H)-oneHCID 108016621-Benzyl-4-methyl-4-phenylpiperidine

Product 1

HCID 226295452a-[4-(4-Methyl-4-phenyl-piperidyl)butyl]-2a,3,4,5-tetrahydrobenz[cd]indole-2(1H)-oneYield 53%

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

1-Benzyl-4-methyl-4-phenylpiperidine (62 mg, 0.24 mmol) was dissolved in ethanol (2 ml). Thereto was added palladium-carbon (10 mg), and the resulting solution was stirred at a room temperature for 17 hours in an atmosphere of argon. The reaction solution was filtered, the solvent was evaporated from the resulting mother liquor under a reduced pressure, and the thus obtained material was dissolved in anhydrous N,N-dimethylformamide (2 ml). The resulting solution was mixed with 2a-(4-bromobutyl)-2a,3,4,5-tetrahydrobenz[cd]indole-2(1H)-one (79 mg, 0.26 mmol) and potassium carbonate (51mg, 0.37mmol) and then the mixture was stirred at 60° C. for 3 hours. The reaction solution was mixed with ethyl acetate and water, and 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 50 mg of the title compound (0.12 mmol, 53% in yield).

Workup

  1. filtrationThe reaction solution was filtered
  2. customthe solvent was evaporated from the resulting mother liquor under a reduced pressure
  3. dissolutionthe thus obtained material was dissolved in anhydrous N,N-dimethylformamide (2 ml)
  4. stirringthe mixture was stirred at 60° C. for 3 hours
  5. extractionthe reaction product was extracted with ethyl acetate
  6. washwashed with saturated brine
  7. dry with materialdried with anhydrous sodium sulfate
  8. customThen the compound obtained by the evaporation of the solvent under a reduced pressure
  9. customwas separated
  10. custompurified by a silica gel column chromatography

Sources & evidence

ORD record
ord-fd66585243f74f00be590f95a360cb58
Source dataset
uspto-grants-2002_03
Patent number
US06355642B1

Reaction notes

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