Trifluoroacetic acid → 4-(4-Fluorophenyl)piperidine

HRID 509272Notes

Reaction equation

HRID 509272 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:13][CH2:12][N:11](C(OC(C)(C)C)=O)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.FC(F)(F)C(O)=O.C([O-])(O)=O.[Na+]>>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:9][CH2:10][NH:11][CH2:12][CH2:13]2)=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 11312007Tert-butyl 4-(4-fluorophenyl)piperidine-1-carboxylate

Product 1

HCID 27591364-(4-Fluorophenyl)piperidineYield 74.4%

Procedure

Tert-butyl 4-(4-fluorophenyl)piperidine-1-carboxylate (46 mg, 0.165 mmol) was dissolved in MC (2 ml), followed by addition of trifluoroacetic acid (1 ml), and then the resulting mixture was stirred at room temperature for 4 hours. The resulting reaction liquid was neutralized by slow addition of a saturated aqueous NaHCO3 solution at 0° C., and then extracted with 5% MeOH/MC (10 ml×2). The organic layer was dried over anhydrous magnesium sulfate, followed by filtration, concentration, and vacuum drying, to obtain 22 mg of colorless oil (74%).

Workup

  1. customThe resulting reaction liquid
  2. extractionextracted with 5% MeOH/MC (10 ml×2)
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. filtrationfollowed by filtration, concentration, and vacuum
  5. customdrying

Sources & evidence

ORD record
ord-39b672bf49794eed967130be70d32cb0
Source dataset
uspto-grants-2015_08
Patent number
US09096571B2

Reaction notes

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