Potassium Carbonate → 1-(4-Oxo-4-[4-fluorophenyl]butyl)-3-(3-methoxyphenyl)piperidine

HRID 1981550Notes

Reaction equation

HRID 1981550 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]2[CH2:14][CH2:13][CH2:12][NH:11][CH2:10]2)[CH:6]=[CH:7][CH:8]=1.[O:15]=[C:16]([C:21]1[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=1)[CH2:17][CH2:18][CH2:19]Cl.C(=O)([O-])[O-].[K+].[K+]>C(C(C)=O)C(C)C>[O:15]=[C:16]([C:21]1[CH:22]=[CH:23][C:24]([F:27])=[CH:25][CH:26]=1)[CH2:17][CH2:18][CH2:19][N:11]1[CH2:12][CH2:13][CH2:14][CH:9]([C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=2)[CH2:10]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 197503-(4-Fluorobenzoyl)propyl chlorideHCID 110742303-(3-Methoxyphenyl)piperidine

Product 1

HCID 137468211-(4-Oxo-4-[4-fluorophenyl]butyl)-3-(3-methoxyphenyl)piperidineYield 39.4%

Reagents, catalysts & solvents 1

HCID 7909Methyl Isobutyl KetoneSolvent

Procedure

A mixture of 1.9 g (0.01 mole) of 3-(3-methoxyphenyl)piperidine, 4.0 g (3.3 ml, 0.02 mole) of 4-oxo-4-(4-fluorophenyl)butyl chloride, 27.6 g (0.20 mole) of potassium carbonate and 75 ml of methyl isobutyl ketone was heated under reflux for ca. 40 hours. The reaction mixture was then poured onto ice-water and the resulting mixture was extracted with ethyl acetate. The combined extracts were washed with water, followed by saturated sodium chloride solution, and then they were dried and evaporated in vacuo. The residue was chromatographed on 250 ml of silica gel, eluting with chloroform/metanol (95:5). The appropriate fractions were combined and evaporated in vacuo to give 1.4 g of the title compound as an amber oil (39% yield).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for ca. 40 hours
  3. additionThe reaction mixture was then poured onto ice-water
  4. extractionthe resulting mixture was extracted with ethyl acetate
  5. washThe combined extracts were washed with water
  6. customthey were dried
  7. customevaporated in vacuo
  8. customThe residue was chromatographed on 250 ml of silica gel
  9. washeluting with chloroform/metanol (95:5)
  10. customevaporated in vacuo

Sources & evidence

ORD record
ord-174006b0bb2f48f482e80c25ff8caed3
Source dataset
uspto-grants-1986_06
Patent number
US04593037

Reaction notes

Loading…