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Potassium Carbonate → HCID 86609404, compound

HRID 1171636
Notes
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Reaction equation

HRID 1171636 reaction equation
Cl.[C:2]([S:5][CH:6]1[CH2:11][CH2:10][NH:9][CH2:8]/[C:7]/1=[CH:12]\[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)(=[O:4])[CH3:3].Br[CH:20]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[F:32])[C:21]([CH:23]1[CH2:25][CH2:24]1)=[O:22].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.C(OCC)(=O)C>[C:2]([S:5][CH:6]1[CH2:11][CH2:10][N:9]([CH:20]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=2[F:32])[C:21]([CH:23]2[CH2:24][CH2:25]2)=[O:22])[CH2:8]/[C:7]/1=[CH:12]\[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)(=[O:4])[CH3:3]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 234358712-Bromo-1-cyclopropyl-2-(2-fluorophenyl)ethanoneHCID 86609405HCID 86609405, compound

Product 1

HCID 86609404HCID 86609404, compoundYield 68%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent
HCID 8857
Ethyl Acetate
Solvent

Procedure

To a solution of (E)-4-(acetylsulfanyl)-3-benzylidene-piperidine hydrochloride and 2-bromo-2-(2-fluorophenyl)-1-cyclopropylethanone (713 mg) in N,N-dimethylformamide (10 ml) was added potassium carbonate (256 mg) under ice-cooling, and the resulting mixture was stirred at room temperature for 2 hours. The reaction mixture was diluted with ethyl acetate and washed with saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous sodium sulfate. The solvent was removed in vacuo, and the residue was purified by chromatography on a silica gel column using a mixed solvent of ethyl acetate and hexane (3:17) as the eluent to afford the title compound (531 mg, yield: 68%) as a yellow oil.

Workup

  1. temperaturecooling
  2. washwashed with saturated aqueous sodium chloride solution
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. customThe solvent was removed in vacuo
  5. customthe residue was purified by chromatography on a silica gel column

Sources & evidence

ORD record
ord-a0105c3362fd4ada972ac89bee4f1a8e
Source dataset
uspto-grants-2010_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07829580B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes