Ethanol → HCID 22930977, compound

HRID 459861Notes

Reaction equation

HRID 459861 reaction equation
C(O)C.[CH3:4][O:5][C:6]1[CH:7]=[C:8]([C:14]2[N:19]=[C:18]([C:20]([N:22]3[CH2:27][CH2:26][N:25]([C:28]4[CH:33]=[CH:32][C:31]([N+:34]([O-])=O)=[CH:30][CH:29]=4)[CH2:24][CH2:23]3)=[O:21])[CH:17]=[CH:16][CH:15]=2)[CH:9]=[CH:10][C:11]=1[O:12][CH3:13].[Cl-].[NH4+]>O>[CH3:4][O:5][C:6]1[CH:7]=[C:8]([C:14]2[N:19]=[C:18]([C:20]([N:22]3[CH2:23][CH2:24][N:25]([C:28]4[CH:29]=[CH:30][C:31]([NH2:34])=[CH:32][CH:33]=4)[CH2:26][CH2:27]3)=[O:21])[CH:17]=[CH:16][CH:15]=2)[CH:9]=[CH:10][C:11]=1[O:12][CH3:13]

Participants

5

Reactant 3

HCID 702EthanolHCID 25517Ammonium ChlorideHCID 22931014HCID 22931014, compound

Product 1

HCID 22930977HCID 22930977, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To an ethanol (70 ml) and water (25 ml) mixed solution of 2.5 g of 1-[6-(3,4-dimethoxyphenyl)pyridine-2-carbonyl]-4-(4-nitrophenyl)piperazine were added 0.15 g of ammonium chloride and 3.1 g of reduced iron, followed by 2 hours of heating under reflux. The reaction solution was filtered through celite and the filtrate was concentrated under reduced pressure. An aqueous sodium hydrogen carbonate solution was added to thus obtained residue, followed by extraction with chloroform. The organic layer was washed with brine and then dried over anhydrous magnesium sulfate, and thereafter, the solvent was evaporated. The residue was purified by silica gel column chromatography (chloroform-methanol) and further, crystallization was carried out from acetonitrile-ethyl acetate to obtain 2.1 g of 1-[6-(3,4-dimethoxyphenyl)pyridine-2-carbonyl]-4-(4-aminophenyl) piperazine as pale pink crystals.

Workup

  1. temperatureof heating
  2. temperatureunder reflux
  3. filtrationThe reaction solution was filtered through celite
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. additionAn aqueous sodium hydrogen carbonate solution was added to thus obtained residue
  6. extractionfollowed by extraction with chloroform
  7. washThe organic layer was washed with brine
  8. dry with materialdried over anhydrous magnesium sulfate
  9. customthe solvent was evaporated
  10. customThe residue was purified by silica gel column chromatography (chloroform-methanol)
  11. customfurther, crystallization

Sources & evidence

ORD record
ord-c5e7f4988eaf4cd6b1179fdb886f8a21
Source dataset
uspto-grants-2007_03
Patent number
US07196080B2

Reaction notes

Loading…