Trifluoroacetic acid → 1-[4-(Trifluoromethoxy)benzenesulfonyl]piperazine

HRID 506862Notes

Reaction equation

HRID 506862 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([S:14]([C:17]2[CH:22]=[CH:21][C:20]([O:23][C:24]([F:27])([F:26])[F:25])=[CH:19][CH:18]=2)(=[O:16])=[O:15])[CH2:10][CH2:9]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[F:27][C:24]([F:25])([F:26])[O:23][C:20]1[CH:21]=[CH:22][C:17]([S:14]([N:11]2[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]2)(=[O:16])=[O:15])=[CH:18][CH:19]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 458629304-(4-Trifluoromethoxy-benzenesulfonyl)-piperazine-1-carboxylic acid tert-butyl ester

Product 1

HCID 20794021-[4-(Trifluoromethoxy)benzenesulfonyl]piperazineYield 87%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a cold (0 C) solution of 4-(4-trifluoromethoxy-benzenesulfonyl)-piperazine-1-carboxylic acid tert-butyl ester (1.15 g, 2.8 mmol) in DCM (3 ml) was added TFA (2 ml). The resulting solution was stirred for 1 hr. Solvent was then removed under reduced pressure. The crude solid was taken-up in AcOEt (15 ml) and washed with NaHCO3 sat (2×5 ml), water (5 ml) and finally with brine (5 ml). The organic layer was dried over MgSO4 and the solvent was removed under vacuo to yield the desired 1-(4-trifluoromethoxy-benzenesulfonyl)-piperazine as a white solid (753 mg, 87% yield).

Workup

  1. customSolvent was then removed under reduced pressure
  2. washwashed with NaHCO3
  3. dry with materialThe organic layer was dried over MgSO4
  4. customthe solvent was removed under vacuo

Sources & evidence

ORD record
ord-9c44250bc06b4969abc709fb7e3ae94f
Source dataset
uspto-grants-2010_08
Patent number
US07786121B2

Reaction notes

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