Potassium Carbonate → HCID 15093864, compound

HRID 1709920Notes

Reaction equation

HRID 1709920 reaction equation
[CH:1]1([CH:7]([C:14]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=2)[CH:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.Cl[CH2:22][CH2:23][CH2:24][O:25][C:26]1[CH:31]=[CH:30][C:29]([C:32](=[O:34])[CH3:33])=[CH:28][C:27]=1[O:35][CH3:36].C(=O)([O-])[O-].[K+].[K+]>C(O)CCC.C(Cl)(Cl)Cl.[I-].[K+]>[CH:1]1([CH:7]([C:14]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=2)[CH:8]2[CH2:13][CH2:12][N:11]([CH2:22][CH2:23][CH2:24][O:25][C:26]3[CH:31]=[CH:30][C:29]([C:32](=[O:34])[CH3:33])=[CH:28][C:27]=3[O:35][CH3:36])[CH2:10][CH2:9]2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 73142644-(3-Chloropropoxy)-3-methoxyacetophenoneHCID 15020366HCID 15020366, compound

Product 1

HCID 15093864HCID 15093864, compoundYield 73.8%

Reagents, catalysts & solvents 3

HCID 4875Potassium IodideCatalystHCID 2631-ButanolSolventHCID 6212ChloroformSolvent

Procedure

A mixture of 4-[cyclohexyl(4-fluorophenyl)methyl]piperidine (5.71 g, 0.0207 mole), 1-[4-(3-chloropropoxy)-3-methoxyphenyl]ethanone (5.03 g, 0.207 mole), and potassium carbonate (5.53 g, 0.04 mole) was heated overnight at reflux in 350 ml of 1-butanol containing potassium iodide (0.2 g). The reaction mixture was cooled to room temperature and filtered. The 1-butanol was removed by rotary evaporation to give a brown oil. This oil was dissolved in chloroform and the chloroform layer was extracted with 5% sodium hydroxide and water. The chloroform layer was dried over sodium sulfate, filtered, and solvent removed to give a brown oil. This oil was subjected to flash chromatography on silica gel. Elution was performed using ethyl acetate, 5% methanol-ethyl acetate, and 10% methanol-ethyl acetate. Separate fractions of similar purity were combined and solvent was removed to give a yellow oil. This oil was dried in vacuo overnight at 80° C. to give 7.36 g (73.8%) of title compound.

Workup

  1. temperaturewas heated overnight
  2. filtrationfiltered
  3. customThe 1-butanol was removed by rotary evaporation
  4. customto give a brown oil
  5. extractionthe chloroform layer was extracted with 5% sodium hydroxide and water
  6. dry with materialThe chloroform layer was dried over sodium sulfate
  7. filtrationfiltered
  8. customsolvent removed
  9. customto give a brown oil
  10. washElution
  11. customsolvent was removed
  12. customto give a yellow oil
  13. customThis oil was dried in vacuo overnight at 80° C.

Sources & evidence

ORD record
ord-35049570d71f4b0c915fba9d66dfe706
Source dataset
uspto-grants-1990_08
Patent number
US04950674

Reaction notes

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