Trifluoroacetic acid → 4-(2-Methoxyphenyl)piperidine

HRID 276888Notes

Reaction equation

HRID 276888 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[O:20][CH3:21])[CH2:10][CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[CH3:21][O:20][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=1[CH:11]1[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 22629567Tert-butyl 4-(2-methoxyphenyl)piperidine-1-carboxylate

Product 1

HCID 5447384-(2-Methoxyphenyl)piperidineYield 104.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-t-Butoxycarbonyl-4-(2-methoxyphenyl)piperidine (120 mg, 0.41 mmol) was dissolved in methylene chloride (2 ml). Thereto was added trifluoroacetic acid (2 ml) and the resulting solution was stirred at a room temperature for 1 hour. The solvent was evaporated under a reduced pressure, and the thus obtained residue was mixed with ethyl acetate. This was washed with 1 N sodium hydroxide aqueous solution and saturated brine in that order, and then the solvent was evaporated under a reduced pressure to obtain 82 mg of the aforementioned compound of interest (0.43 mmol, 104% in yield).

Workup

  1. customThe solvent was evaporated under a reduced pressure
  2. additionthe thus obtained residue was mixed with ethyl acetate
  3. washThis was washed with 1 N sodium hydroxide aqueous solution and saturated brine in that order
  4. customthe solvent was evaporated under a reduced pressure
  5. customto obtain

Sources & evidence

ORD record
ord-076a3c9d858d4dcfadc6fa1418c107db
Source dataset
uspto-grants-2002_03
Patent number
US06355642B1

Reaction notes

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