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

HRID 1639072Notes

Reaction equation

HRID 1639072 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 mole) of mechanically stirred 1-benzylpiperazine was added 10.0 g (0.07 mole) of 4-nitrofluorobenzene. After 10 minutes the mixture solidified. The yellow solid was suspended in 50 ml of ethyl acetate and ethereal hydrogen chloride 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° C.) to give 9.8 g (47%) of yellow solid, m.p. 115°-118° C.

Workup

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

Sources & evidence

ORD record
ord-799c4af83782488db6ac964aa4d8cfff
Source dataset
uspto-grants-1989_11
Patent number
US04882330

Reaction notes

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