Sodium Dithionite → 1-(4-Aminophenyl)-4-(4-pyridyl)piperazine

HRID 427445

Reaktionsgleichung

Reaktionsgleichung von HRID 427445
S(S([O-])=O)([O-])=O.[Na+].[Na+].[N:9]1[CH:14]=[CH:13][C:12]([N:15]2[CH2:20][CH2:19][N:18]([C:21]3[CH:26]=[CH:25][C:24]([N+:27]([O-])=O)=[CH:23][CH:22]=3)[CH2:17][CH2:16]2)=[CH:11][CH:10]=1>O.CO>[N:9]1[CH:14]=[CH:13][C:12]([N:15]2[CH2:16][CH2:17][N:18]([C:21]3[CH:26]=[CH:25][C:24]([NH2:27])=[CH:23][CH:22]=3)[CH2:19][CH2:20]2)=[CH:11][CH:10]=1

Komponenten

5

Edukt 2

HCID 24489Sodium DithioniteHCID 10924082Piperazine,1-(4-nitrophenyl)-4-(4-pyridinyl)-

Produkt 1

HCID 108904611-(4-Aminophenyl)-4-(4-pyridyl)piperazineAusbeute 81,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

A solution of sodium dithionite (2.5 g) in water (10 ml) was added to a warmed solution of 1-(4-pyridyl)-4-(4-nitrophenyl)piperazine (0.551 g) in methanol (50 ml) and the mixture was allowed to reflux for 2 hours. The methanol was removed by evaporation and the resulting concentrated solution was basified with solid Na2SO4. The organic material was extracted into ethyl acetate, washed with water, brine, dried (Na2SO4) and evaporated to give 1-(4-pyridyl)-4-(4-aminophenyl)piperazine (0.4 g) as an oil. NMR: (CDCl3) 3.14(t,4H), 3.48(t, 4H), 6.68(m,4H), 6.85(d,2H), 8.31(bd,2H): MS: m z 255 (MH)−.

Aufarbeitung

  1. temperatureto reflux for 2 hours
  2. customThe methanol was removed by evaporation
  3. extractionThe organic material was extracted into ethyl acetate
  4. washwashed with water, brine
  5. dry with materialdried (Na2SO4)
  6. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-06923bc1add44b71b1ca06c2553823a0
Quelldatensatz
uspto-grants-2001_11
Patentnummer
US06313127B1

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