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

HRID 2365442Notes

Reaction equation

HRID 2365442 reaction equation
[F:1][C:2]([F:27])([F:26])[O:3][C:4]1[CH:9]=[CH:8][C:7]([S:10]([N:13]2[CH2:18][CH2:17][N:16](C(OC(C)(C)C)=O)[CH2:15][CH2:14]2)(=[O:12])=[O:11])=[CH:6][CH:5]=1.Cl.O1CCOCC1>C(Cl)Cl>[F:27][C:2]([F:1])([F:26])[O:3][C:4]1[CH:9]=[CH:8][C:7]([S:10]([N:13]2[CH2:14][CH2:15][NH:16][CH2:17][CH2:18]2)(=[O:12])=[O:11])=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 458629304-(4-Trifluoromethoxy-benzenesulfonyl)-piperazine-1-carboxylic acid tert-butyl ester2×

Product 1

HCID 20794021-[4-(Trifluoromethoxy)benzenesulfonyl]piperazineYield 84.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1,1-Dimethylethyl 4-({4-[(trifluoromethyl)oxy]phenyl}sulfonyl)-1-piperazinecarboxylate (may be prepared as described in Intermediate 10; 5.450 g, 13.28 mmol) was dissolved in DCM (80 ml) and then 4M hydrochloric acid in dioxane (33.2 mL, 133 mmol) was added at room temperature and the reaction mixture was stirred for two hours. The reaction mixture was partitioned between DCM and aqueous sodium bicarbonate (30 ml). The organic phase was washed with further sodium bicarbonate (2×20 ml) and water (2×20 ml). The aqueous phase (pH 1) was basified by adding sodium hydroxide then the aqueous phase was extracted with DCM (2×20 ml). The solvent was removed under vacuum to give the title compound (3.5 g) as a white solid.

Workup

  1. customThe reaction mixture was partitioned between DCM and aqueous sodium bicarbonate (30 ml)
  2. washThe organic phase was washed with further sodium bicarbonate (2×20 ml) and water (2×20 ml)
  3. additionby adding sodium hydroxide
  4. extractionthe aqueous phase was extracted with DCM (2×20 ml)
  5. customThe solvent was removed under vacuum

Sources & evidence

ORD record
ord-7c535fd624d0404da61212a7324ff69f
Source dataset
uspto-grants-2014_04
Patent number
US08697703B2

Reaction notes

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