Ethyl trifluoroacetate → 1-Trifluoroacetyl-4-hydroxy-4-phenylpiperidine

HRID 65969Notes

Reaction equation

HRID 65969 reaction equation
[OH:1][C:2]1([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.[F:14][C:15]([F:22])([F:21])[C:16](OCC)=[O:17]>>[F:14][C:15]([F:22])([F:21])[C:16]([N:5]1[CH2:6][CH2:7][C:2]([OH:1])([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:3][CH2:4]1)=[O:17]

Participants

3

Reactant 2

HCID 9794Ethyl trifluoroacetateHCID 963874-Phenylpiperidin-4-ol

Product 1

HCID 14465131-Trifluoroacetyl-4-hydroxy-4-phenylpiperidine

Procedure

The starting material is prepared as follows: The mixture of 25 g of 4-hydroxy-4-phenylpiperidine and 50 ml of ethyl trifluoroacetate is refluxed overnight and evaporated. The residue is taken up in benzene, the solution washed with 1N hydrochloric acid, dried and evaporated. The residue is recrystallized from ethyl acetate-petroleum ether, to yield the 1-trifluoroacetyl-4-hydroxy-4-phenylpiperidine melting at 123°-125°.

Workup

  1. customThe starting material is prepared
  2. temperatureis refluxed overnight
  3. customevaporated
  4. washthe solution washed with 1N hydrochloric acid
  5. customdried
  6. customevaporated
  7. customThe residue is recrystallized from ethyl acetate-petroleum ether

Sources & evidence

ORD record
ord-85b342c49efc47bd97c2025dfa1e28f5
Source dataset
uspto-grants-1978_12
Patent number
US04129655

Reaction notes

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