HCID 23081330, compound → HCID 17825545, compound

HRID 856069Notes

Reaction equation

HRID 856069 reaction equation
[F:1][C:2]([F:25])([F:24])[C:3]1[CH:23]=[CH:22][C:6]([CH2:7][O:8][CH:9]2[CH2:14][CH2:13][N:12](C(OC(C)(C)C)=O)[CH2:11][CH2:10]2)=[CH:5][CH:4]=1>C(Cl)Cl.FC(F)(F)C(O)=O>[F:25][C:2]([F:1])([F:24])[C:3]1[CH:23]=[CH:22][C:6]([CH2:7][O:8][CH:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)=[CH:5][CH:4]=1

Participants

4

Reactant 1

HCID 23081330HCID 23081330, compound

Product 1

HCID 17825545HCID 17825545, compoundYield 100.2%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

Tert-butyl 4-(4-trifluoromethylbenzyloxy)-piperidine-1-carboxylate (2.56 g, 7.12 mmol) prepared in Reference Example 122 was dissolved in methylene chloride (20 ml), to which trifluoroacetic acid (10 ml) was added dropwise, and the mixture was stirred at room temperature for 5 hours. The reaction mixture was concentrated under reduced pressure, and the residue was then dissolved in methylene chloride. This solution was neutralized with 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-trifluoromethylbenzyloxy)piperidine (1.85 g, yield 99%) as a white powder.

Workup

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

Sources & evidence

ORD record
ord-7c94c5d3849b495e9ab4c773d5cf0c10
Source dataset
uspto-grants-2007_08
Patent number
US07262212B2

Reaction notes

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