Trifluoroacetic acid → HCID 22629547, compound

HRID 276909Notes

Reaction equation

HRID 276909 reaction equation
C(O[C:6]([N:8]1[CH2:13][CH2:12][C:11]([O:20][CH3:21])([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O.[CH3:29][N:30]1[C:38]2[CH:37]=[CH:36][CH:35]=[C:34]3[CH2:39][CH2:40][CH2:41][C:32]([CH2:42][CH2:43][CH2:44]CBr)([C:33]=23)[C:31]1=[O:47].C(=O)([O-])[O-].[K+].[K+]>ClCCl.C(OCC)(=O)C.O>[CH3:21][O:20][C:11]1([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH2:10][CH2:9][N:8]([CH2:6][CH2:44][CH2:43][CH2:42][C:32]23[CH2:41][CH2:40][CH2:39][C:34]4[C:33]2=[C:38]([CH:37]=[CH:36][CH:35]=4)[N:30]([CH3:29])[C:31]3=[O:47])[CH2:13][CH2:12]1

Participants

8

Reactant 4

HCID 6422Trifluoroacetic acidHCID 11430Potassium CarbonateHCID 110563612a-(4-Bromobutyl)-1-methyl-2a,3,4,5-tetrahydro-1H-benz[cd]indol-2-oneHCID 22629553HCID 22629553, compound

Product 1

HCID 22629547HCID 22629547, compoundYield 22.1%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

1-t-Butoxycarbonyl-4-methoxy-4-phenyl-piperidine (510 mg, 1.7 mmol) was dissolved in dichloromethane (2 ml). Thereto was added trifluoroacetic acid (4 ml), and the resulting solution was stirred at a room temperature for 30 minutes. The reaction solution was diluted with ethyl acetate, washed with sodium hydroxide aqueous solution (1 N) and dried with anhydrous sodium sulfate. The solvent was evaporated under a reduced pressure, and the thus obtained material was dissolved in anhydrous N,N-dimethylformamide (2 ml). Then the resulting solution was mixed with 1-methyl-2a-(4-bromobutyl)-2a,3,4,5-tetrahydrobenz[cd]indole-2(1H) -one (450 mg, 1.4 mmol) and potassium carbonate (290 mg, 2.1 mmol) and 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 79 mg of the title compound (0.31 mmol, 18% in yield).

Workup

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

Sources & evidence

ORD record
ord-a7c13e6597314dbea7086ab7a021bbc6
Source dataset
uspto-grants-2002_03
Patent number
US06355642B1

Reaction notes

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