Trifluoroacetic acid → 4-(4-(Trifluoromethyl)phenoxy)piperidine

HRID 856035Notes

Reaction equation

HRID 856035 reaction equation
[F:1][C:2]([F:24])([F:23])[C:3]1[CH:22]=[CH:21][C:6]([O:7][CH:8]2[CH2:13][CH2:12][N:11](C(OC(C)(C)C)=O)[CH2:10][CH2:9]2)=[CH:5][CH:4]=1.FC(F)(F)C(O)=O>C(Cl)Cl>[F:24][C:2]([F:1])([F:23])[C:3]1[CH:22]=[CH:21][C:6]([O:7][CH:8]2[CH2:9][CH2:10][NH:11][CH2:12][CH2:13]2)=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 22052586tert-Butyl 4-(4-(trifluoromethyl)phenoxy)piperidine-1-carboxylate

Product 1

HCID 36883924-(4-(Trifluoromethyl)phenoxy)piperidineYield 91%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Tert-butyl 4-(4-trifluoromethylphenoxy)piperidine-1-carboxylate (1.13 g, 3.27 mmol) prepared in Reference Example 37 was dissolved in methylene chloride (10 ml). To which trifluoroacetic acid (10 ml) was added dropwise and the mixture was stirred at room temperature for 5 hours. After the reaction mixture was concentrated under reduced pressure, the residue was again dissolved in methylene chloride. The solution was neutralized with a sodium hydroxide aqueous solution, and the mixture was extracted with methylene chloride. The extract was washed with brine, dried over magnesium sulfate, and then filtered. The filtrate was concentrated under reduced pressure to afford 4-(4-trifluoromethylphenoxy)piperidine (727 mg, yield 91%) as a white powder.

Workup

  1. concentrationAfter the reaction mixture was concentrated under reduced pressure
  2. dissolutionthe residue was again dissolved in methylene chloride
  3. extractionthe mixture was extracted with methylene chloride
  4. washThe extract was washed with brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-77b08985d42946d181c5e04629a6c86e
Source dataset
uspto-grants-2007_08
Patent number
US07262212B2

Reaction notes

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