Water → HCID 69107964, compound

HRID 1838259Notes

Reaction equation

HRID 1838259 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([N:9]2[C@H:14]([CH3:15])[CH2:13][N:12]([C:16]([NH:18][C:19]3[CH:24]=[CH:23][C:22]([N+:25]([O-])=O)=[CH:21][CH:20]=3)=[O:17])[C@@H:11]([CH3:28])[CH2:10]2)=[CH:5][C:4]=1[C:29]([F:32])([F:31])[F:30])#[N:2].O.[Cl-].[NH4+]>CO.[Fe]>[NH2:25][C:22]1[CH:21]=[CH:20][C:19]([NH:18][C:16]([N:12]2[CH2:13][C@@H:14]([CH3:15])[N:9]([C:6]3[CH:7]=[CH:8][C:3]([C:1]#[N:2])=[C:4]([C:29]([F:32])([F:31])[F:30])[CH:5]=3)[CH2:10][C@@H:11]2[CH3:28])=[O:17])=[CH:24][CH:23]=1

Participants

6

Reactant 3

HCID 962WaterHCID 25517Ammonium Chloride2×HCID 69108563HCID 69108563, compound

Product 1

HCID 69107964HCID 69107964, compound

Reagents, catalysts & solvents 2

HCID 23925IronCatalyst2×HCID 887MethanolSolvent

Procedure

A 450 mg portion of trans-4-(4-cyano-3-trifluoromethylphenyl)-2,5-dimethyl-4′-nitropiperazine-1-carboxanilide synthesized in Example 1-4 was dissolved in 8 ml of methanol, and the solution was mixed with 4 ml of water, 280 mg of iron powder and 30 mg of ammonium chloride and heated under reflux for 5 hours. The reaction solution was again mixed with 280 mg of iron powder and 30 mg of ammonium chloride and further heated under reflux for 2 hours. The reaction solution was filtered through celite, and the solvent in the filtrate was evaporated under reduced pressure. The residue was dissolved in ethyl acetate, washed with water and saturated brine in that order and then dried over sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by a silica gel column chromatography (methanol-chloroform) to obtain 260 mg of the title compound as colorless crystals.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 5 hours
  3. temperaturefurther heated
  4. temperatureunder reflux for 2 hours
  5. filtrationThe reaction solution was filtered through celite
  6. customthe solvent in the filtrate was evaporated under reduced pressure
  7. dissolutionThe residue was dissolved in ethyl acetate
  8. washwashed with water and saturated brine in that order
  9. dry with materialdried over sodium sulfate
  10. customThe solvent was evaporated under reduced pressure
  11. customthe residue was purified by a silica gel column chromatography (methanol-chloroform)

Sources & evidence

ORD record
ord-f9ea1b5c17d84d17a766abdb67ace211
Source dataset
uspto-grants-2004_01
Patent number
US06673799B1

Reaction notes

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