Water → HCID 58606586, compound

HRID 1744512Notes

Reaction equation

HRID 1744512 reaction equation
[Cl-].[NH4+].O.[N+:4]([C:7]1[CH:12]=[CH:11][C:10]([N:13]2[CH2:18][C@@H:17]([CH3:19])[N:16]([CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])[C@@H:15]([CH3:26])[CH2:14]2)=[C:9]([C:27]#[N:28])[CH:8]=1)([O-])=O>[Fe].C(O)C>[NH2:4][C:7]1[CH:12]=[CH:11][C:10]([N:13]2[CH2:18][C@@H:17]([CH3:19])[N:16]([CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])[C@@H:15]([CH3:26])[CH2:14]2)=[C:9]([C:27]#[N:28])[CH:8]=1

Participants

6

Reactant 3

HCID 962WaterHCID 25517Ammonium ChlorideHCID 69648868HCID 69648868, compound

Product 1

HCID 58606586HCID 58606586, compoundYield 96.3%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent2×

Conditions

Temperature
65 °C

Procedure

Ammonium chloride (1.2 g) and iron powder (6.1 g) were added to a mixed solvent of water (90 ml) and ethanol (270 ml), and the mixture was heated to 65° C. Then, ethanol solution (20 ml) containing ethyl cis-4-(4-nitro-2-cyanophenyl)-2,6-dimethylpiperazin-1-ylacetate (10.8 g) was dropwise added in parts over 20 min and the mixture was stirred at a refluxing temperature for 1 h. The reaction mixture was ice-cooled and filtrated. The solvent was evaporated under reduced pressure. To the residue was added aqueous sodium hydroxide solution and the mixture was extracted with toluene. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate, after which the solvent was evaporated under reduced pressure. n-Hexane was added to the residue to allow crystallization. The crystals were recrystallized from a mixed solvent of diisopropyl ether-n-hexane to give the title compound (9.5 g), melting point: 45° C.

Workup

  1. additionwas dropwise added in parts over 20 min
  2. temperaturecooled
  3. filtrationfiltrated
  4. customThe solvent was evaporated under reduced pressure
  5. additionTo the residue was added aqueous sodium hydroxide solution
  6. extractionthe mixture was extracted with toluene
  7. washThe organic layer was washed with saturated brine
  8. dry with materialdried over anhydrous sodium sulfate
  9. customafter which the solvent was evaporated under reduced pressure
  10. additionn-Hexane was added to the residue
  11. customcrystallization
  12. customThe crystals were recrystallized from a mixed solvent of diisopropyl ether-n-hexane

Sources & evidence

ORD record
ord-1693ee0e626e4c5a8a0e2fcbf452f7c1
Source dataset
uspto-grants-2006_03
Patent number
US07015218B1

Reaction notes

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