p-Fluoronitrobenzene → 4-Nitrophenyl-cis-2,5-dimethylpiperazine

HRID 476564

Reaction equation

HRID 476564 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=1.[CH3:11][C@H:12]1[CH2:17][NH:16][C@@H:15]([CH3:18])[CH2:14][NH:13]1.C(=O)(O)[O-].[Na+]>C(O)CCCC>[N+:8]([C:5]1[CH:6]=[CH:7][C:2]([N:13]2[CH2:14][C@H:15]([CH3:18])[NH:16][CH2:17][C@@H:12]2[CH3:11])=[CH:3][CH:4]=1)([O-:10])=[O:9]

Participants

5

Reactant 3

HCID 9590p-FluoronitrobenzeneHCID 61380(2S,5S)-2,5-dimethylpiperazineHCID 516892Sodium Bicarbonate

Product 1

HCID 703830304-Nitrophenyl-cis-2,5-dimethylpiperazine

Reagents, catalysts & solvents 1

HCID 62761-PentanolSolvent

Procedure

A mixture of 4-fluoronitrobenzene (30.34 g, 0.22 mole), cis-2,5-dimethylpiperazine (25 g, 0.22 mole) and sodium bicarbonate (24 g, 0.28 mole) in n-pentanol (150 ml) was heated under nitrogen at 90°-100° for 18 hours. After filtration, the n-pentanol was removed under reduced pressure and the residue was partitioned between methylene chloride and water. The organic phase was separated, washed again with water, dried over magnesium sulphate, and concentrated under reduced pressure. The residue was triturated with ice water to yield a yellow solid. The solid was filtered off and dried to yield the title compound, m.p. 93°-4° (37 g, 71%).

Workup

  1. temperaturewas heated under nitrogen at 90°-100° for 18 hours
  2. filtrationAfter filtration
  3. customthe n-pentanol was removed under reduced pressure
  4. customthe residue was partitioned between methylene chloride and water
  5. customThe organic phase was separated
  6. washwashed again with water
  7. dry with materialdried over magnesium sulphate
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was triturated with ice water
  10. customto yield a yellow solid
  11. filtrationThe solid was filtered off
  12. customdried

Sources & evidence

ORD record
ord-39c6d35731454baca426491e193a62b4
Source dataset
uspto-grants-1989_12
Patent number
US04885294

Linked notes

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