1-(4-Fluorophenyl)-4-[(4-nitrophenyl)sulfonyl]piperazine → HCID 21314924, compound

HRID 237017Notes

Reaction equation

HRID 237017 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10]([N:13]2[CH2:18][CH2:17][N:16]([C:19]3[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=3)[CH2:15][CH2:14]2)(=[O:12])=[O:11])=[CH:6][CH:5]=1)([O-])=O>[Pt]=O.C(Cl)(Cl)Cl>[NH2:1][C:4]1[CH:9]=[CH:8][C:7]([S:10]([N:13]2[CH2:18][CH2:17][N:16]([C:19]3[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=3)[CH2:15][CH2:14]2)(=[O:12])=[O:11])=[CH:6][CH:5]=1

Participants

4

Reactant 1

HCID 10685021-(4-Fluorophenyl)-4-[(4-nitrophenyl)sulfonyl]piperazine

Product 1

HCID 21314924HCID 21314924, compoundYield 47.1%

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 6212ChloroformSolvent

Procedure

A mixture of 5.00 g (0.0137 m) of 1-[(p-nitrophenyl)sulfonyl]-4-(p-fluorophenyl)piperazine, 0.2 g of platinum oxide, and 150 ml of chloroform is shaken under hydrogen on a Parr hydrogenation apparatus for one hour. The mixture is then filtered through a sintered glass funnel containing activated carbon and sand to remove the catalyst. The filtrate is concentrated in vacuo and then extracted with methylene chloride/aqueous sodium bicarbonate. The organic layer is filtered through anhydrous sodium sulfate and taken to dryness. The residue is crystallized from methanol to give 2.16 g of 1-[(p-aminophenyl)sulfonyl]-4-(p-fluorophenyl)piperazine containing a minor impurity. Recrystallization from methanol gives an analytical sample with a melting point of 180.5°-181.5° C.

Workup

  1. filtrationThe mixture is then filtered through a sintered glass funnel
  2. additioncontaining activated carbon and sand
  3. customto remove the catalyst
  4. concentrationThe filtrate is concentrated in vacuo
  5. extractionextracted with methylene chloride/aqueous sodium bicarbonate
  6. filtrationThe organic layer is filtered through anhydrous sodium sulfate
  7. customThe residue is crystallized from methanol

Sources & evidence

ORD record
ord-c0dabf1b92554995b61bf588bccbc459
Source dataset
uspto-grants-1979_06
Patent number
US04159331

Reaction notes

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