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Potassium Carbonate → HCID 9887186, compound

HRID 2301073
Notes
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Reaction equation

HRID 2301073 reaction equation
[CH2:1]1[C:6]2[NH:7][C:8]3[C:13]([C:5]=2[CH2:4][CH2:3][NH:2]1)=[CH:12][CH:11]=[CH:10][CH:9]=3.C(=O)([O-])[O-].[K+].[K+].Br[CH2:21][CH2:22][CH2:23][CH2:24][C:25]12[CH2:36][CH2:35][CH2:34][C:32]3[C:33]1=[C:28]([CH:29]=[CH:30][CH:31]=3)[NH:27][C:26]2=[O:37]>CN(C=O)C>[CH2:1]1[C:6]2[NH:7][C:8]3[C:13]([C:5]=2[CH2:4][CH2:3][N:2]1[CH2:21][CH2:22][CH2:23][CH2:24][C:25]12[CH2:36][CH2:35][CH2:34][C:32]4[C:33]1=[C:28]([CH:29]=[CH:30][CH:31]=4)[NH:27][C:26]2=[O:37])=[CH:12][CH:11]=[CH:10][CH:9]=3
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 107838Tetrahydro-beta-carbolineHCID 105908942a-(4-Bromobutyl)-2a,3,4,5-tetrahydrobenz[cd]indole-2(1H)-one

Product 1

HCID 9887186HCID 9887186, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A 168 mg (0.98 mmol) portion of 2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole and 269 mg (1.96 mmol) of potassium carbonate were added to 3 ml of DMF solution containing 150 mg (0.49 mmol) of 2a-(4-bromobutyl)-2a,3,4,5-tetrahydro-1H-benz[cd]indol-2-one and stirred overnight at room temperature. The reaction solution was extracted with chloroform and washed with water. After drying (Na2SO4), the solvent was removed by evaporation under a reduced pressure and the residue was recrystallized from acetone to obtain 98 mg of the title compound (48% in yield). An oily material obtained by concentrating the mother liquid was purified by a silica gel column chromatography (30 cc; elution by chloroform-methanol=15:1) to obtain 73 mg of the title compound (38% in yield).

Workup

  1. extractionThe reaction solution was extracted with chloroform
  2. washwashed with water
  3. dry with materialAfter drying (Na2SO4)
  4. customthe solvent was removed by evaporation under a reduced pressure
  5. customthe residue was recrystallized from acetone

Sources & evidence

ORD record
ord-1d01663c648f4db7a57e11b0ec9370f0
Source dataset
uspto-grants-2002_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06498251B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes