Acetic Acid → 1-(4-Oxo-4-[4-fluorophenyl]butyl)-3-(3-hydroxyphenyl)piperidine

HRID 1981542Notes

Reaction equation

HRID 1981542 reaction equation
[O:1]=[C:2]([C:20]1[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=1)[CH2:3][CH2:4][CH2:5][N:6]1[CH2:11][CH2:10][CH2:9][CH:8]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([O:18]C)[CH:13]=2)[CH2:7]1.Br.C(O)(=O)C.C(=O)([O-])[O-].[K+].[K+]>C(Cl)(Cl)Cl.O>[O:1]=[C:2]([C:20]1[CH:21]=[CH:22][C:23]([F:26])=[CH:24][CH:25]=1)[CH2:3][CH2:4][CH2:5][N:6]1[CH2:11][CH2:10][CH2:9][CH:8]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([OH:18])[CH:13]=2)[CH2:7]1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 260Hydrogen BromideHCID 11430Potassium CarbonateHCID 137468211-(4-Oxo-4-[4-fluorophenyl]butyl)-3-(3-methoxyphenyl)piperidine

Product 1

HCID 136049101-(4-Oxo-4-[4-fluorophenyl]butyl)-3-(3-hydroxyphenyl)piperidineYield 39.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent

Procedure

A mixture of 1.4 g (4 mmole) of 1-(4-oxo-4-[4-fluorophenyl]butyl)-3-(3-methoxyphenyl)piperidine, 10 ml of 48% aqueous hydrobromic acid and 5 ml of glacial acetic acid was heated under reflux for ca. 20 hours. The reaction mixture was then poured onto a mixture of ice and water. The resulting mixture was basified with potassium carbonate and then it was extracted with ethyl acetate. The extracts were washed with water, followed by saturated sodium chloride solution, and then they were dried (MgSO4) and evaporated in vacuo. The residue was purified by chromatography on 150 ml of silica gel, eluting with chloroform/methanol (95:5). The product was then recrystallized from chloroform to give 540 mg (30% yield) of the title compound as a chloroform solvate, m.p. 77°-78° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for ca. 20 hours
  3. extractionit was extracted with ethyl acetate
  4. washThe extracts were washed with water
  5. dry with materialthey were dried (MgSO4)
  6. customevaporated in vacuo
  7. customThe residue was purified by chromatography on 150 ml of silica gel
  8. washeluting with chloroform/methanol (95:5)
  9. customThe product was then recrystallized from chloroform

Sources & evidence

ORD record
ord-e23d946253f54c2bb116fec562b0576e
Source dataset
uspto-grants-1986_06
Patent number
US04593037

Reaction notes

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