Trifluoroacetic acid → 1-(Propylsulfonyl)piperazine

HRID 2167352Notes

Reaction equation

HRID 2167352 reaction equation
[CH2:1]([S:4]([N:7]1[CH2:12][CH2:11][N:10](C(OC(C)(C)C)=O)[CH2:9][CH2:8]1)(=[O:6])=[O:5])[CH2:2][CH3:3].FC(F)(F)C(O)=O>C(Cl)Cl>[CH2:1]([S:4]([N:7]1[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]1)(=[O:5])=[O:6])[CH2:2][CH3:3]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 46743467913952-86-0

Product 1

HCID 8322411-(Propylsulfonyl)piperazine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirring ice-cold solution of tert-butyl 4-(propylsulfonyl)piperazine-1-carboxylate (2, 15.70 g, 53.69 mmol) in CH2Cl2 (200 mL) was slowly added trifluoroacetic acid (21.4 mL, 268.45 mmol). The mixture stirred at room temperature for 16 h under an atmosphere of N2. The mixture was washed with 2 N NaOH (3×50 mL), H2O (50 mL), brine (50 mL), dried (Na2SO4), filtered, and concentrated under reduced pressure to afford 1-(propylsulfonyl)piperazine (3) as a crystalline solid (10.30 g quantitative): 1H NMR (500 MHz, CDCl3) δ 7.91 (d, J=1.7 Hz, 1H), 7.48 (d, J=1.6 Hz, 1H), 7.21 (m, 1H), 7.14 (s, 1H), 7.09 (s, 1H), 3.96 (s, 3H), 3.75 (s, 3H).

Workup

  1. washThe mixture was washed with 2 N NaOH (3×50 mL), H2O (50 mL), brine (50 mL)
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-05abf57f55714c3ca4a626fedc9bd818
Source dataset
uspto-grants-2015_06
Patent number
US09045445B2

Reaction notes

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