p-Fluoronitrobenzene → HCID 178511611, compound

HRID 22938Notes

Reaction equation

HRID 22938 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7](F)=[CH:6][CH:5]=1)([O-:3])=[O:2].[C@H:11]1([NH2:18])[CH2:16][CH2:15][C@H:14]([NH2:17])[CH2:13][CH2:12]1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C(=O)C>[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([NH:17][C@H:14]2[CH2:15][CH2:16][C@H:11]([NH2:18])[CH2:12][CH2:13]2)=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 9590p-FluoronitrobenzeneHCID 11430Potassium CarbonateHCID 178511674HCID 178511674, compound

Product 1

HCID 178511611HCID 178511611, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
144 °C

Procedure

A N,N-dimethylacetamide (30 ml) solution containing 4-nitrofluorobenzene (1.69 g) and trans-1,4-cyclohexanediamine (4.1 g) was stirred at 144° C. for 3 days. After cooling, an aqueous saturated potassium carbonate solution was added to the reaction solution, and the reaction mixture was extracted with ethyl acetate. The extract was dried over anhydrous potassium carbonate, and then, the solvent was removed under reduced pressure. The residue was purified by silica gel flash column chromatography (solvent: chloroform-methanol-ammonia (90:10:1)), and the solvent was removed to obtain trans-N-(4-nitrophenyl)-1,4-cyclohexanediamine (Reference Example 3-41 in Table 5) (2.31 g).

Workup

  1. temperatureAfter cooling
  2. extractionthe reaction mixture was extracted with ethyl acetate
  3. dry with materialThe extract was dried over anhydrous potassium carbonate
  4. customthe solvent was removed under reduced pressure
  5. customThe residue was purified by silica gel flash column chromatography (solvent: chloroform-methanol-ammonia (90:10:1))
  6. customthe solvent was removed

Sources & evidence

ORD record
ord-a63b99af0ecf4446926d9168dae24558
Source dataset
uspto-grants-2005_02
Patent number
US06849622B2

Reaction notes

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