Ethanol → HCID 86594431, compound

HRID 459873Notes

Reaction equation

HRID 459873 reaction equation
C([OH:3])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][C@@H:26]([CH3:28])[N:25]([C:29]4[CH:34]=[CH:33][C:32]([N+:35]([O-])=O)=[CH:31][CH:30]=4)[CH2:24][C@@H:23]3[CH3:38])=[O:21])[CH:17]=[CH:16][CH:15]=2)[CH:9]=[CH:10][C:11]=1[O:12][CH3:13].[Cl-:39].[NH4+]>O>[OH2:3].[ClH:39].[CH3:4][O:5][C:6]1[CH:7]=[C:8]([C:14]2[N:19]=[C:18]([C:20]([N:22]3[C@H:23]([CH3:38])[CH2:24][N:25]([C:29]4[CH:30]=[CH:31][C:32]([NH2:35])=[CH:33][CH:34]=4)[C@@H:26]([CH3:28])[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 69159683HCID 69159683, compound

Product 1

HCID 86594431HCID 86594431, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To an ethanol (37 ml) and water (13 ml) mixed solution of 1.42 g of (±)-trans-1-[6-(3,4-dimethoxyphenyl)pyridine-2-carbonyl]-2,5-dimethyl-4-(4-nitrophenyl)piperazine were added 0.16 g of ammonium chloride and 1.66 g of reduced iron, followed by 0.5 hour of heating under reflux. The reaction solution was filtered through celite and the filtrate was concentrated under reduced pressure. An aqueous saturated 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 the obtained compound was treated with a 4M hydrogen chloride/ethyl acetate solution to form its salt. Then, the solvent was evaporated and the residue was washed with ethyl acetate to obtain 582 mg of (±)-trans-4-{4-[6-(3,4-dimethoxyphenyl)pyridine-2-carbonyl]-2,5-dimethylpiperazin-1-yl}aniline hydrochloride hydrate as pale yellow 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 saturated 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. additionthe obtained compound was treated with a 4M hydrogen chloride/ethyl acetate solution
  12. customto form its salt
  13. customThen, the solvent was evaporated
  14. washthe residue was washed with ethyl acetate

Sources & evidence

ORD record
ord-5bf53c1a69f54c95a735a006feaf8b64
Source dataset
uspto-grants-2007_03
Patent number
US07196080B2

Reaction notes

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