Potassium Carbonate → HCID 15093866, compound

HRID 1709918Notes

Reaction equation

HRID 1709918 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=2)[CH:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)=[CH:4][CH:3]=1.Cl[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][O:29][C:30]1[CH:35]=[CH:34][C:33]([C:36](=[O:38])[CH3:37])=[CH:32][C:31]=1[O:39][CH3:40].C(=O)([O-])[O-].[K+].[K+].CO.C(OCC)(=O)C>C(O)CCC.C(Cl)(Cl)Cl.C(OCC)(=O)C.[I-].[K+]>[F:21][C:18]1[CH:17]=[CH:16][C:15]([CH:8]([C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)[CH:9]2[CH2:14][CH2:13][N:12]([CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][O:29][C:30]3[CH:35]=[CH:34][C:33]([C:36](=[O:38])[CH3:37])=[CH:32][C:31]=3[O:39][CH3:40])[CH2:11][CH2:10]2)=[CH:20][CH:19]=1

Participants

9

Reactant 4

HCID 11430Potassium CarbonateHCID 132505444-[Bis(4-fluorophenyl)methyl]piperidineHCID 14407180HCID 14407180, compoundHCID 21584119Ethylacetate methanol

Product 1

HCID 15093866HCID 15093866, compoundYield 54.4%

Reagents, catalysts & solvents 4

HCID 4875Potassium IodideCatalystHCID 2631-ButanolSolventHCID 6212ChloroformSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

A mixture of 4-[bis(4-fluorophenyl)methyl]piperidine (7.90 g, 0.0275 mole), 1-[4-(6-chlorohexyloxy)-3-methoxyphenyl]ethanone (7.82 g, 0.025 mole), and potassium carbonate (5.54 g, 0.04 mole) was heated overnight at reflux in 400 ml of 1-butanol containing potassium iodide (0.2 g). The mixture was cooled to room temperature and filtered. Butanol was removed by rotary evaporation. The brown oil obtained was dissolved in chloroform and extracted several times with water. The chloroform layer was dried over sodium sulfate, filtered, and solvent removed to give a brown oil. This oil was dissolved in ethyl acetate and subjected to flask chromatography on silica gel using ethyl acetate and 5% methanol-ethyl acetate for elution. Fractions of similar purity were combined and solvent removed to give an oil. The oil was dried at 80° C. overnight in vacuo to give 7.28 g (54.4% yield) of title compound as a light brown oil.

Workup

  1. temperaturewas heated overnight
  2. filtrationfiltered
  3. customButanol was removed by rotary evaporation
  4. customThe brown oil obtained
  5. extractionextracted several times with water
  6. dry with materialThe chloroform layer was dried over sodium sulfate
  7. filtrationfiltered
  8. customsolvent removed
  9. customto give a brown oil
  10. customsubjected to flask
  11. washfor elution
  12. customsolvent removed
  13. customto give an oil
  14. customThe oil was dried at 80° C. overnight in vacuo

Sources & evidence

ORD record
ord-ce3b5c3df7774da5848a5758ec8d8c3c
Source dataset
uspto-grants-1990_08
Patent number
US04950674

Reaction notes

Loading…