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Potassium Carbonate → HCID 178501112, compound

HRID 538054
Notes
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Reaction equation

HRID 538054 reaction equation
C([O-])([O-])=O.[K+].[K+].F[C:8]1[CH:13]=[C:12]([C:14]([F:17])([F:16])[F:15])[CH:11]=[CH:10][C:9]=1[N+:18]([O-:20])=[O:19].[CH3:21][O:22][C:23]([C@H:25]1[CH2:30][CH2:29][C@H:28]([CH2:31][NH2:32])[CH2:27][CH2:26]1)=[O:24]>CN(C=O)C>[CH3:21][O:22][C:23]([C@H:25]1[CH2:30][CH2:29][C@H:28]([CH2:31][NH:32][C:8]2[CH:13]=[C:12]([C:14]([F:17])([F:16])[F:15])[CH:11]=[CH:10][C:9]=2[N+:18]([O-:20])=[O:19])[CH2:27][CH2:26]1)=[O:24]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 37221693-fluoro-4-nitrobenzotrifluorideHCID 178501118HCID 178501118, compound

Product 1

HCID 178501112HCID 178501112, compoundYield 86.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

K2CO3 (1.6 g, 11.7 mmol), 2-Fluoro-1-nitro-4-trifluoromethyl-benzene (1.22 g, 5.8 mmol) and trans-4-Aminomethyl-cyclohexanecarboxylic acid methyl ester (1.00 g, 5.84 mmol) were dissolved in DMF (10 ml). The mixture was stirred at 50° C. overnight. The solvent was removed under reduced pressure and the crude product dissolved in DCM (15 ml) and washed with water (20 ml) and then with a solution of citric acid (1M, 5 ml). The organic solution was dried over Na2SO4, filtered and the solvent removed by evaporation to give solid material. This was washed with cyclohexane and then with isopropyl ether and purified by silica column using DCM/cyclo hexane (1:1) as eluent. 1.8 g (yield 86%) of the title compound were isolated.

Workup

  1. customThe solvent was removed under reduced pressure
  2. dissolutionthe crude product dissolved in DCM (15 ml)
  3. washwashed with water (20 ml)
  4. dry with materialThe organic solution was dried over Na2SO4
  5. filtrationfiltered
  6. customthe solvent removed by evaporation
  7. customto give solid material
  8. washThis was washed with cyclohexane
  9. customwith isopropyl ether and purified by silica column

Sources & evidence

ORD record
ord-2d482fafe8e649b8841a8f7e5390fded
Source dataset
uspto-grants-2014_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08865704B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes