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

HRID 476564

Reaktionsgleichung

Reaktionsgleichung von HRID 476564
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]

Komponenten

5

Edukt 3

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 62761-PentanolLösungsmittel

Versuchsvorschrift

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%).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-39c6d35731454baca426491e193a62b4
Quelldatensatz
uspto-grants-1989_12
Patentnummer
US04885294

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