Trifluoroacetic acid → 1-(Methylsulfonyl)piperazine

HRID 2377296Notes

Reaction equation

HRID 2377296 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].FC(F)(F)C(O)=O>ClCCl>[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)piperazine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of Example 1013 (8.2 g, 28.5 mmol) in dichloromethane (40 mL) was added trifluoroacetic acid (30 mL) at about 0° C. The mixture was stirred at room temperature for about 4 h and was then concentrated under vacuum. The residue was basified with sodium carbonate and was extracted with dichloromethane. The combined organic extracts were dried over Na2SO4, filtered and concentrated under vacuum to provide the desired product. 1H NMR (300 MHz, CDCL3): δ 2.80 (s, 3H), 3.00 (t, J=7.0 Hz, 4H), 3.21 (t, J=7.0 Hz, 4H).

Workup

  1. concentrationwas then concentrated under vacuum
  2. extractionwas extracted with dichloromethane
  3. dry with materialThe combined organic extracts were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-cb152b86f41b42ad98f6a2ebfa966dd3
Source dataset
uspto-grants-2008_12
Patent number
US07468371B2

Reaction notes

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