Water → 1-[N-(2-nitrophenyl)-2-aminoethyl]-4-(2-methoxyphenyl)piperazine

HRID 1420569Notes

Reaction equation

HRID 1420569 reaction equation
Cl[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N+:8]([O-:10])=[O:9].[NH2:11][CH2:12][CH2:13][N:14]1[CH2:19][CH2:18][N:17]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[O:26][CH3:27])[CH2:16][CH2:15]1.C(=O)([O-])[O-].[K+].[K+].O>C(O)CCC>[N+:8]([C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[NH:11][CH2:12][CH2:13][N:14]1[CH2:15][CH2:16][N:17]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[O:26][CH3:27])[CH2:18][CH2:19]1)([O-:10])=[O:9]

Participants

6

Reactant 4

HCID 962WaterHCID 69451-Chloro-2-nitrobenzeneHCID 11430Potassium CarbonateHCID 103991861-(2-Aminoethyl)-4-(2-methoxyphenyl)piperazine

Product 1

HCID 224820891-[N-(2-nitrophenyl)-2-aminoethyl]-4-(2-methoxyphenyl)piperazineYield 32.1%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A mixture of 3.03 g of 2-chloronitrobenzene, 4.52 g of 1-(2-aminoethyl)-4-(2-methoxyphenyl)piperazine, and 3.18 g of anhydrous potassium carbonate in 30 mL of n-butanol was stirred for 32 h at reflux. After cooling, the mixture was poured into H2O, then extracted with EtOAc and the organic phase dried on Na2SO4. The crude obtained by evaporating the solvent was purified by flash chromatography (EtOAc-petrolium ether 4:6) and the residue obtained after evaporation of the solvents was taken up with Et2O, stirred and filtered giving 2.2 g (31%) of the title compound. Melting point: 117-118° C.

Workup

  1. temperatureat reflux
  2. temperatureAfter cooling
  3. extractionextracted with EtOAc
  4. customthe organic phase dried on Na2SO4
  5. customThe crude obtained
  6. customby evaporating the solvent
  7. customwas purified by flash chromatography (EtOAc-petrolium ether 4:6)
  8. customthe residue obtained
  9. customafter evaporation of the solvents
  10. stirringstirred
  11. filtrationfiltered

Sources & evidence

ORD record
ord-5622dec4f522420698c3772d87370ae0
Source dataset
uspto-grants-2000_06
Patent number
US06071920

Reaction notes

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