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

HRID 427445

Reaction equation

HRID 427445 reaction equation
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

Participants

5

Reactant 2

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

Product 1

HCID 108904611-(4-Aminophenyl)-4-(4-pyridyl)piperazineYield 81.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

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)−.

Workup

  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

Sources & evidence

ORD record
ord-06923bc1add44b71b1ca06c2553823a0
Source dataset
uspto-grants-2001_11
Patent number
US06313127B1

Linked notes

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