Reaction #51216

Reaction equation

4-nitrofluorobenzene

trans-1,4-cyclohexanediamine

potassium carbonate

→

trans-N-(4-nitrophenyl)-1,4-cyclohexanediamine

Yield 82.0%

Solvents

N,N-dimethylacetamide

Conditions

Workup

1. 1
   TemperatureAfter cooling
2. 2
   Extractionthe reaction mixture was extracted with ethyl acetate
3. 3
   DryingThe extract was dried over anhydrous potassium carbonate
4. 4
   Otherthe solvent was removed under reduced pressure
5. 5
   OtherThe residue was purified by silica gel flash column chromatography (solvent: chloroform-methanol-ammonia (90:10:1))
6. 6
   Otherthe solvent was removed

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).

Source