Potassium Carbonate → HCID 178492437, compound

HRID 538050Notes

Reaction equation

HRID 538050 reaction equation
C([O-])([O-])=O.[K+].[K+].F[C:8]1[CH:13]=[C:12]([O:14][CH3:15])[CH:11]=[CH:10][C:9]=1[N+:16]([O-:18])=[O:17].[CH3:19][O:20][C:21]([C@H:23]1[CH2:28][CH2:27][C@H:26]([CH2:29][NH2:30])[CH2:25][CH2:24]1)=[O:22]>CN(C=O)C>[CH3:19][O:20][C:21]([C@H:23]1[CH2:28][CH2:27][C@H:26]([CH2:29][NH:30][C:8]2[CH:13]=[C:12]([O:14][CH3:15])[CH:11]=[CH:10][C:9]=2[N+:16]([O-:18])=[O:17])[CH2:25][CH2:24]1)=[O:22]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 5656543-Fluoro-4-nitroanisoleHCID 178501118HCID 178501118, compound

Product 1

HCID 178492437HCID 178492437, compoundYield 91.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

K2CO3 (9.04 g, 65.5 mmol) was added to a solution of 2-Fluoro-4-methoxy-1-nitro-benzene (5.6 g, 32.7 mmol) in DMF (20 ml). The mixture was stirred at room temperature for 30 minutes and then trans-4-Aminomethyl-cyclohexanecarboxylic acid methyl ester (5.60 g, 32.7 mmol) was added. The reaction mixture was heated for 2 hours at 50° C. and then at room temperature overnight. The solvent was removed under reduced pressure and the crude product dissolved in DCM (150 ml) and washed with water (2×150 ml) and then with a solution of citric acid (2×150 ml). The organic solution was dried over Na2SO4, filtered and the solvent removed by evaporation to give 9.6 g of the titled compound.

Workup

  1. temperatureThe reaction mixture was heated for 2 hours at 50° C.
  2. customat room temperature
  3. customovernight
  4. customThe solvent was removed under reduced pressure
  5. dissolutionthe crude product dissolved in DCM (150 ml)
  6. washwashed with water (2×150 ml)
  7. dry with materialThe organic solution was dried over Na2SO4
  8. filtrationfiltered
  9. customthe solvent removed by evaporation

Sources & evidence

ORD record
ord-6ec85b8aa8184cc78593775fa81ce7a4
Source dataset
uspto-grants-2014_10
Patent number
US08865704B2

Reaction notes

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