1-(Bis(4-fluorophenyl)methyl)piperazine → HCID 22111636, compound

HRID 565771Notes

Reaction equation

HRID 565771 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][NH:26][S:27]([CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35]Cl)(=[O:29])=[O:28]>C(N(C(C)C)C(C)C)C>[OH:22][CH2:23][CH2:24][CH2:25][NH:26][S:27]([CH2:30][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:29])=[O:28]

Participants

4

Reactant 2

HCID 1529321-(Bis(4-fluorophenyl)methyl)piperazineHCID 22111543HCID 22111543, compound

Product 1

HCID 22111636HCID 22111636, compoundYield 95.8%

Reagents, catalysts & solvents 1

HCID 81531DiisopropylethylamineSolvent

Procedure

1-[Bis(4-fluorophenyl)methyl]piperazine (576.7 mg, 2.00 mmol) and N-(3-hydroxypropyl)-6-chlorohexanesulfonamide (515.6 mg, 2.00 mmol) were refluxed in N-ethyldiisopropylamine (2 ml) for 6 hours. The reaction mixture was concentrated in vacuc, 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-(3-hydroxypropyl)-6-[4-[bis(4-fluorophenyl)methyl]-1-piperazinyl]hexanesulfonamide (976.6 mg) as a pale yellow oil (95.8%).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuc, 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-0c7947ec719e47099a73874e6c74d31b
Source dataset
uspto-grants-2001_01
Patent number
US06172228B2

Reaction notes

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