Trifluoroacetic acid → 1-(Methylsulfonyl)piperazine

HRID 916380Notes

Reaction equation

HRID 916380 reaction equation
[CH3:1][S:2]([N:5]1[CH2:10][CH2:9][N:8](C(OC(C)(C)C)=O)[CH2:7][CH2:6]1)(=[O:4])=[O:3].C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH3:1][S:2]([N:5]1[CH2:10][CH2:9][NH:8][CH2:7][CH2:6]1)(=[O:4])=[O:3]

Participants

4

Reactant 2

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

Product 1

HCID 7091611-(Methylsulfonyl)piperazineYield 50.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of tert-butyl 4-(methylsulfonyl)piperazine-1-carboxylate (7 g) in methylene chloride (150 ml) containing TFA (35 ml) was stirred for 2 hours at ambient temperature. The volatiles were removed under vacuum and the resultant residue was partitioned between methylene chloride and 2N aqueous sodium hydroxide. The organic phase was separated and washed with brine, dried over magnesium sulphate and evaporated to give 1-(methylsulfonyl)piperazine (2.18 g).

Workup

  1. customThe volatiles were removed under vacuum
  2. customthe resultant residue was partitioned between methylene chloride and 2N aqueous sodium hydroxide
  3. customThe organic phase was separated
  4. washwashed with brine
  5. dry with materialdried over magnesium sulphate
  6. customevaporated

Sources & evidence

ORD record
ord-7c40523ffe454f81adf44d8c70e78bf7
Source dataset
uspto-grants-2007_09
Patent number
US07268230B2

Reaction notes

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