Trifluoroacetic acid → 1-(Methylsulfonyl)piperazine

HRID 2068024Notes

Reaction equation

HRID 2068024 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-(methylsulphonyl)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-(methylsulphonyl)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-71b29db507144912afd4152fc1abbdc1
Source dataset
uspto-grants-2012_10
Patent number
US08293902B2

Reaction notes

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