1-(Bis(4-fluorophenyl)methyl)piperazine → HCID 22111579, compound

HRID 565773Notes

Reaction equation

HRID 565773 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=2)[N:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)=[CH:4][CH:3]=1.[OH:22][CH2:23][CH2:24][CH2:25][CH2:26][NH:27][S:28]([CH2:31][CH2:32][CH2:33][CH2:34][CH2:35]Cl)(=[O:30])=[O:29]>C(N(C(C)C)C(C)C)C>[OH:22][CH2:23][CH2:24][CH2:25][CH2:26][NH:27][S:28]([CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][N:12]1[CH2:11][CH2:10][N:9]([CH:8]([C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=2)[C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=2)[CH2:14][CH2:13]1)(=[O:30])=[O:29]

Participants

4

Reactant 2

HCID 1529321-(Bis(4-fluorophenyl)methyl)piperazineHCID 22111542HCID 22111542, compound

Product 1

HCID 22111579HCID 22111579, compoundYield 91.7%

Reagents, catalysts & solvents 1

HCID 81531DiisopropylethylamineSolvent

Procedure

1-[Bis(4-fluorophenyl)methyl]piperazine (576.7 mg, 2.00 mmol) and N-(4-hydroxybutyl)-5-chloropentanesulfonamide (515.6 mg, 2.00 mmol) were refluxed in N-ethyldiisopropylamine (2 ml) for 6 hours. The reaction mixture was concentrated in vacuo, and water was added thereto. The mixture was extracted with chloroform. The chloroform layer was washed with water, and dried over anhydrous magnesium sulfate. Subsequently, the solvent was removed by evaporation in vacuo. The resulting crude product was purified by column chromatography on silica gel with chloroform-methanol (20:1), to give N-(4-hydroxybutyl)-5-[4-[bis(4-fluorophenyl)methyl]-1-piperazinyl]pentanesulfonamide (934.3 mg) as a pale yellow oil (91.7%).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo, and water
  2. additionwas added
  3. extractionThe mixture was extracted with chloroform
  4. washThe chloroform layer was washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customSubsequently, the solvent was removed by evaporation in vacuo
  7. customThe resulting crude product was purified by column chromatography on silica gel with chloroform-methanol (20:1)

Sources & evidence

ORD record
ord-bb74922c72e944e69a9888ef97b426dc
Source dataset
uspto-grants-2001_01
Patent number
US06172228B2

Reaction notes

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