Trifluoroacetic acid → 4-(2-Methoxyphenyl)-1,2,3,6-tetrahydropyridine

HRID 276889Notes

Reaction equation

HRID 276889 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][C:11](O)([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[C:11]1[CH2:12][CH2:13][NH:8][CH2:9][CH:10]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 226295651-Boc-4-(2-methoxyphenyl)-4-hydroxypiperidine

Product 1

HCID 155426354-(2-Methoxyphenyl)-1,2,3,6-tetrahydropyridineYield 101.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-t-Butoxycarbonyl-4-hydroxy-4-(2-methoxyphenyl)piperidine (240 mg, 0.78 mmol) was dissolved in methylene chloride (4 ml). Thereto was added trifluoroacetic acid (4 ml) and the resulting solution was stirred at room temperature for 1 hour. The solvent was evaporated under a reduced pressure, and ethyl acetate was added to the thus obtained residue. 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 150 mg of the aforementioned compound of interest (0.78 mmol, 100% in yield).

Workup

  1. customThe solvent was evaporated under a reduced pressure, and ethyl acetate
  2. additionwas added to the thus obtained residue
  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-13100be761794a9da1d04f111cf890f5
Source dataset
uspto-grants-2002_03
Patent number
US06355642B1

Reaction notes

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