Trifluoroacetic acid → 4-[5-Fluoro-2-(3,3,5,5-tetramethylcyclohex-1-enyl)phenyl]piperidine

HRID 32267Notes

Reaction equation

HRID 32267 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[CH:19]=[C:18]([F:20])[CH:17]=[CH:16][C:15]=2[C:21]2[CH2:26][C:25]([CH3:28])([CH3:27])[CH2:24][C:23]([CH3:30])([CH3:29])[CH:22]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[F:20][C:18]1[CH:17]=[CH:16][C:15]([C:21]2[CH2:26][C:25]([CH3:28])([CH3:27])[CH2:24][C:23]([CH3:30])([CH3:29])[CH:22]=2)=[C:14]([CH:11]2[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]2)[CH:19]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 597693864-[5-Fluoro-2-(3,3,5,5-tetramethylcyclohex-1-enyl)phenyl]piperidine-1-carboxylic acid t-butyl ester

Product 1

HCID 231425804-[5-Fluoro-2-(3,3,5,5-tetramethylcyclohex-1-enyl)phenyl]piperidineYield 118.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-[5-fluoro-2-(3,3,5,5-tetramethylcyclohex-1-enyl)phenyl]piperidine-1-carboxylic acid t-butyl ester (245 mg, 0.59 mmol) produced in Example (106f) in dichloromethane (3 mL) was added trifluoroacetic acid (3 mL), followed by stirring for 30 minutes at room temperature. The reaction mixture was concentrated under reduced pressure, and then saturated aqueous solution of sodium hydrogencarbonate was added to the obtained residue and extraction was performed with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, and the filtrate was concentrated under reduced pressure to give 220 mg of a crude product of the title compound as a light yellow solid.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionsaturated aqueous solution of sodium hydrogencarbonate was added to the obtained residue and extraction
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-b8a16d69ca7f447aa026bd51e9c7b879
Source dataset
uspto-grants-2008_09
Patent number
US07425554B2

Reaction notes

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