Trifluoroacetic acid → HCID 70873620, compound

HRID 2172212Notes

Reaction equation

HRID 2172212 reaction equation
FC(F)(F)C(O)=O.C(OC([N:15]1[CH2:20][CH2:19][CH:18]([CH2:21][CH2:22][O:23][C:24]2[CH:29]=[CH:28][C:27]([O:30][C:31]([F:34])([F:33])[F:32])=[CH:26][CH:25]=2)[CH2:17][CH2:16]1)=O)(C)(C)C>ClCCl>[F:33][C:31]([F:32])([F:34])[O:30][C:27]1[CH:26]=[CH:25][C:24]([O:23][CH2:22][CH2:21][CH:18]2[CH2:17][CH2:16][NH:15][CH2:20][CH2:19]2)=[CH:29][CH:28]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 708737904-[2-(4-Trifluoromethoxyphenoxy)ethyl]piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 70873620HCID 70873620, compoundYield 101.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (40 ml) was added to a dichloromethane solution (40 ml) of 4-[2-(4-trifluoromethoxyphenoxy)ethyl]piperidine-1-carboxylic acid tert-butyl ester (18.6 g), and the mixture was stirred at room temperature for 5 hours. The mixture was concentrated under reduced pressure, and ice water was added to the resulting residue. The result was treated with 6 N sodium hydroxide aqueous solution, followed by extraction with ethyl acetate. The organic layer was washed with a saturated sodium chloride aqueous solution and dried over magnesium sulfate. The solvent was concentrated to dryness under reduced pressure to afford the title compound as a white powder (14 g).

Workup

  1. concentrationThe mixture was concentrated under reduced pressure, and ice water
  2. additionwas added to the resulting residue
  3. additionThe result was treated with 6 N sodium hydroxide aqueous solution
  4. extractionfollowed by extraction with ethyl acetate
  5. washThe organic layer was washed with a saturated sodium chloride aqueous solution
  6. dry with materialdried over magnesium sulfate
  7. concentrationThe solvent was concentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-9ad0de0e4dae403ca8516d2755a09cb8
Source dataset
uspto-grants-2015_06
Patent number
US09051333B2

Reaction notes

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