Trifluoroacetic acid → 4-[2-(Trifluoromethyl)phenoxy]piperidine

HRID 561188Notes

Reaction equation

HRID 561188 reaction equation
FC(F)(F)C(O)=O.[F:8][C:9]([F:31])([F:30])[C:10]1[CH:29]=[CH:28][CH:27]=[CH:26][C:11]=1[O:12][CH:13]1[CH2:18][CH2:17][N:16](C(OC(C)(C)C)=O)[CH2:15][CH2:14]1>C(Cl)Cl>[F:31][C:9]([F:8])([F:30])[C:10]1[CH:29]=[CH:28][CH:27]=[CH:26][C:11]=1[O:12][CH:13]1[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 46941590Tert-butyl 4-(2-(trifluoromethyl)phenoxy)piperidine-1-carboxylate

Product 1

HCID 50187904-[2-(Trifluoromethyl)phenoxy]piperidine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (26.3 mL, 342 mmol) was added to a solution of tert-butyl 4-[2-(trifluoromethyl)phenoxy]piperidine-1-carboxylate (29.5 g, 85 mmol) in CH2Cl2 (171 mL). The mixture was stirred at room temperature for 16 h. The solvent was removed by evaporation. The residue was diluted with EtOAc (200 mL), washed with 2 N NaOH (3×100 mL), brine, dried over Na2SO4, and evaporated to give the title compound as an oil.

Workup

  1. customThe solvent was removed by evaporation
  2. additionThe residue was diluted with EtOAc (200 mL)
  3. washwashed with 2 N NaOH (3×100 mL), brine
  4. dry with materialdried over Na2SO4
  5. customevaporated

Sources & evidence

ORD record
ord-651f15b3e36345b1b0a76ac5aa3df6c0
Source dataset
uspto-grants-2011_11
Patent number
US08063224B2

Reaction notes

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