Hydrochloric Acid → 1-Benzyl-4-(4-nitrophenyl)piperazine

HRID 1533899Notes

Reaction equation

HRID 1533899 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N+:14]([C:17]1[CH:22]=[CH:21][C:20](F)=[CH:19][CH:18]=1)([O-:16])=[O:15].Cl>C(OCC)(=O)C>[N+:14]([C:17]1[CH:22]=[CH:21][C:20]([N:11]2[CH2:12][CH2:13][N:8]([CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[CH2:9][CH2:10]2)=[CH:19][CH:18]=1)([O-:16])=[O:15]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 9590p-FluoronitrobenzeneHCID 759941-Benzylpiperazine

Product 1

HCID 27474271-Benzyl-4-(4-nitrophenyl)piperazineYield 47%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To 12.5 g (0.07 mol) of mechanically stirred 1-benzylpiperazine was added 10.0 g (0.07 mol) of 4-nitrofluorobenzene. After 10 minutes of a mildly exothermic reaction, the mixture solidified. The yellow solid was suspended in 50 mL of ethyl acetate and ethereal HCl was slowly added to the stirring mixture under a nitrogen atmosphere. The solid was collected (filtration) and partitioned between 10% sodium hydroxide solution and benzene. The benzene layer was washed with ten 100 mL portions of water, dried with anhydrous magnesium sulfate and concentrated under reduced pressure to give a yellow oil. Upon cooling, the oil crystallized. The solid was recrystallized from 2-propanol/petroleum ether (60°-110°) to give 9.8 g (47%) of yellow solid, mp 115°-118° C.

Workup

  1. customAfter 10 minutes of a mildly exothermic reaction
  2. customThe solid was collected
  3. filtration(filtration)
  4. custompartitioned between 10% sodium hydroxide solution and benzene
  5. washThe benzene layer was washed with ten 100 mL portions of water
  6. dry with materialdried with anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customto give a yellow oil
  9. temperatureUpon cooling
  10. customthe oil crystallized
  11. customThe solid was recrystallized from 2-propanol/petroleum ether (60°-110°)

Sources & evidence

ORD record
ord-24cab5e768d9448a98c6c70b5c377bbb
Source dataset
uspto-grants-1992_02
Patent number
US05086055

Reaction notes

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