Trifluoroacetic acid → 4-{Bis[4-(trifluoromethoxy)phenyl]methyl}piperidin-4-ol

HRID 1642027Notes

Reaction equation

HRID 1642027 reaction equation
[F:1][C:2]([F:37])([F:36])[O:3][C:4]1[CH:9]=[CH:8][C:7]([CH:10]([C:25]2[CH:30]=[CH:29][C:28]([O:31][C:32]([F:35])([F:34])[F:33])=[CH:27][CH:26]=2)[C:11]2([OH:24])[CH2:16][CH2:15][N:14](C(OC(C)(C)C)=O)[CH2:13][CH2:12]2)=[CH:6][CH:5]=1.FC(F)(F)C(O)=O>C(Cl)Cl>[F:34][C:32]([F:33])([F:35])[O:31][C:28]1[CH:27]=[CH:26][C:25]([CH:10]([C:7]2[CH:8]=[CH:9][C:4]([O:3][C:2]([F:37])([F:1])[F:36])=[CH:5][CH:6]=2)[C:11]2([OH:24])[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]2)=[CH:30][CH:29]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86633668Tert-butyl 4-{bis[4-(trifluoromethoxy)phenyl]methyl}-4-hydroxypiperidine carboxylate

Product 1

HCID 166562744-{Bis[4-(trifluoromethoxy)phenyl]methyl}piperidin-4-ol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A mixture of 3.0 grams (0.0057 mole) of tert-butyl 4-{bis[4-(trifluoromethoxy)phenyl]methyl}-4-hydroxypiperidine carboxylate and 25 mL of methylene chloride was chilled in a wet ice bath. A solution of 2.63 mL trifluoro acetic acid and 5 mL methylene chloride was added dropwise to the reaction mixture during a 5-minute period. The wet ice bath was removed and the reaction mixture was allowed to warm to ambient temperature. The reaction mixture was then warmed to reflux, and allowed to cool to ambient temperature. The reaction mixture was concentrated under reduced pressure. The residue can then be dissolved in 100 mL methylene chloride and reacted with 200 mL of an aqueous solution saturated with sodium carbonate. The methylene chloride layer can then be separated, dried over magnesium sulfate, filtered and concentrated under reduced pressure to yield the subject compound.

Workup

  1. temperaturewas chilled in a wet ice bath
  2. customThe wet ice bath was removed
  3. temperatureThe reaction mixture was then warmed
  4. temperatureto reflux
  5. temperatureto cool to ambient temperature
  6. concentrationThe reaction mixture was concentrated under reduced pressure
  7. dissolutionThe residue can then be dissolved in 100 mL methylene chloride
  8. customreacted with 200 mL of an aqueous solution saturated with sodium carbonate
  9. customThe methylene chloride layer can then be separated
  10. dry with materialdried over magnesium sulfate
  11. filtrationfiltered
  12. concentrationconcentrated under reduced pressure
  13. customto yield the subject compound

Sources & evidence

ORD record
ord-a67177cedbe745cd9217d351e96e9391
Source dataset
uspto-grants-2012_02
Patent number
US08119563B2

Reaction notes

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