Trifluoroacetic acid → 1-(Methylsulfonyl)piperazine

HRID 491582Notes

Reaction equation

HRID 491582 reaction equation
C([N:8]1[CH2:13][CH2:12][N:11]([S:14]([CH3:17])(=[O:16])=[O:15])[CH2:10][CH2:9]1)(OC(C)(C)C)=O.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH3:17][S:14]([N:11]1[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]1)(=[O:16])=[O:15]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 4496004Tert-butyl 4-(methylsulfonyl)piperazine-1-carboxylate

Product 1

HCID 7091611-(Methylsulfonyl)piperazine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-Boc-4-Methanesulfonyl-piperazine (10.4 g, 39.5 mmol) was dissolved in 50 mL CH2Cl2 and treated with 15 mL TFA. After stirring at RT for 18 h, the reaction was concentrated in vacuo, dissolved in 1 N HCl and extracted twice with CH2Cl2. The aqueous layer was basified to pH>12 with solid NaOH, then extracted twice with EtOAc. The EtOAc layer was washed with a mix of brine and 1N NaOH, dried over Na2SO4, filtered, and concentrated in vacuo, to yield the title compound as a clear liquid. MS (MH+)=NA; Calc'd 164.23 for C5H12N2O2S.

Workup

  1. concentrationthe reaction was concentrated in vacuo
  2. dissolutiondissolved in 1 N HCl
  3. extractionextracted twice with CH2Cl2
  4. extractionextracted twice with EtOAc
  5. washThe EtOAc layer was washed with
  6. additiona mix of brine and 1N NaOH
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c8f328810a8d494fbf00c4ab7e5b78f2
Source dataset
uspto-grants-2009_05
Patent number
US07531553B2

Reaction notes

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