Hydrochloric Acid → 1-[4-(Trifluoromethyl)benzenesulfonyl]piperazine

HRID 418272Notes

Reaction equation

HRID 418272 reaction equation
[F:1][C:2]([F:26])([F:25])[C:3]1[CH:8]=[CH:7][C:6]([S:9]([N:12]2[CH2:17][CH2:16][N:15](C(OC(C)(C)C)=O)[CH2:14][CH2:13]2)(=[O:11])=[O:10])=[CH:5][CH:4]=1.Cl>O1CCOCC1.O.C(Cl)Cl>[F:26][C:2]([F:1])([F:25])[C:3]1[CH:4]=[CH:5][C:6]([S:9]([N:12]2[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]2)(=[O:10])=[O:11])=[CH:7][CH:8]=1

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 466817241,1-Dimethylethyl 4-{[4-(trifluoromethyl)phenyl]sulfonyl}-1-piperazinecarboxylate

Product 1

HCID 25545781-[4-(Trifluoromethyl)benzenesulfonyl]piperazine

Reagents, catalysts & solvents 3

HCID 962WaterCatalystHCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent2×

Procedure

To a solution of 1,1-dimethylethyl 4-{[4-(trifluoromethyl)phenyl]sulfonyl}-1-piperazinecarboxylate in 1,4-dioxane (100 ml) was added 4M HCl in 1,4-dioxane (50 ml, 200 mmol) and 3 drops of distilled water. The reaction mixture was stirred overnight and then reduced to dryness in vacuo. The residue was dissolved in DCM (200 ml) and washed with 2M aq. NaOH (50 ml), twice. The organic layer was dried over dried magnesium sulphate, the insolubles removed by filtration, and filtrate reduced to dryness in vacuo to yield the title compound (6.60 g) as a pale yellow solid.

Workup

  1. washwashed with 2M aq. NaOH (50 ml)
  2. dry with materialThe organic layer was dried over dried magnesium sulphate
  3. customthe insolubles removed by filtration, and filtrate

Sources & evidence

ORD record
ord-a89be73e991a430283502ec0474d7db1
Source dataset
uspto-grants-2012_01
Patent number
US08093249B2

Reaction notes

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