p-Fluoronitrobenzene → Piperazine,1-(4-nitrophenyl)-4-(4-pyridinyl)-

HRID 427444

Reaktionsgleichung

Reaktionsgleichung von HRID 427444
[H-].[Na+].[N:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)=[CH:5][CH:4]=1.F[C:16]1[CH:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[CH:18][CH:17]=1>CN(C)C=O>[N:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH2:10][CH2:11][N:12]([C:16]3[CH:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[CH:18][CH:17]=3)[CH2:13][CH2:14]2)=[CH:5][CH:4]=1

Komponenten

5

Edukt 3

HCID 9590p-FluoronitrobenzeneHCID 24758Sodium hydrideHCID 705171-(4-Pyridyl)piperazine

Produkt 1

HCID 10924082Piperazine,1-(4-nitrophenyl)-4-(4-pyridinyl)-

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

Sodium hydride (0.5 g) (45-55% dispersion in oil was added to a solution of 1-(4-pyridyl)piperazine (0.9 g) in dry dimethylformamide (10 ml) at ambient temperature and stirred for 30 minutes. After this time, 4-fluoronitrobenzene (0.65 ml) was added slowly and the temperature raised to 70° C. The mixture was maintained at this temperature for 2 hours. The reaction mixture was then quenched by pouring into water and acidifying with aq 2N HCl solution to pH 1. The acidic layer was washed with diethyl ether and then basified with aq 2N.NaOH solution. The resulting precipitate was filtered, washed with water, dissolved in methanol, filtered through phase separator paper and evaporated to dryness. The resulting crude material was recrystallised from methanol/ether to give 1-(4-pyridyl)-4-(4nitrophenyl)piperazine (0.64 g) as an oil, NMR: (CDCl3) 3.61(q,8H), 6.58(d,2H), 6.81(d,2H), 8.16(d,2H), 8.33(bs,2H); MS: m/z 285 (MH)+.

Aufarbeitung

  1. temperatureThe mixture was maintained at this temperature for 2 hours
  2. customThe reaction mixture was then quenched
  3. additionby pouring into water and acidifying with aq 2N HCl solution to pH 1
  4. washThe acidic layer was washed with diethyl ether
  5. filtrationThe resulting precipitate was filtered
  6. washwashed with water
  7. dissolutiondissolved in methanol
  8. filtrationfiltered through phase
  9. customevaporated to dryness
  10. customThe resulting crude material was recrystallised from methanol/ether

Quellen und Nachweise

ORD-Eintrag
ord-43bbc1851bc345588cd50715cb30982a
Quelldatensatz
uspto-grants-2001_11
Patentnummer
US06313127B1

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