1-Phenylpiperazine → 2-(4-Phenylpiperazinylethyl)nitrobenzene

HRID 280511Notes

Reaction equation

HRID 280511 reaction equation
Br[CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[N+:10]([O-:12])=[O:11].[C:13]1([N:19]2[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>C(O)C>[C:13]1([N:19]2[CH2:24][CH2:23][N:22]([CH2:2][CH2:3][C:4]3[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=3[N+:10]([O-:12])=[O:11])[CH2:21][CH2:20]2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 70961-PhenylpiperazineHCID 123638782-Nitrophenethyl bromide

Product 1

HCID 132176892-(4-Phenylpiperazinylethyl)nitrobenzene

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A mixture comprising 0.1 mol 2-(2-bromoethyl)nitrobenzene, 0.23 mol N-phenylpiperazine, and 300 cc absolute ethanol was heated for 15 hr with agitation and refluxing of the ethanol. The alcohol was then removed by evaporation. The residue of the evaporation was dissolved in water. This was then extracted with ether. The ether phase was washed with fresh water, and then dried over sodium sulfate, after which the ether was evaporated off. The excess N-phenylpiperazine was removed by distillation. The distillation residue was recrystallized in methanol, yielding 2-(4-phenylpiperazinylethyl)nitrobenzene with m.p.=76° C.

Workup

  1. customThe alcohol was then removed by evaporation
  2. customThe residue of the evaporation
  3. dissolutionwas dissolved in water
  4. extractionThis was then extracted with ether
  5. washThe ether phase was washed with fresh water
  6. dry with materialdried over sodium sulfate
  7. customafter which the ether was evaporated off
  8. customThe excess N-phenylpiperazine was removed by distillation
  9. customThe distillation residue was recrystallized in methanol

Sources & evidence

ORD record
ord-7ead0dea930341d8ac53def8f26ded2c
Source dataset
uspto-grants-1986_05
Patent number
US04590193

Reaction notes

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