HCID 22247960, compound → HCID 22247975, compound

HRID 890046Notes

Reaction equation

HRID 890046 reaction equation
C([N:8]1[CH2:13][CH2:12][CH:11]([C:14](=[O:27])[CH2:15][C:16]2[C:21]([C:22]([F:25])([F:24])[F:23])=[CH:20][CH:19]=[CH:18][C:17]=2[F:26])[CH2:10][CH2:9]1)C1C=CC=CC=1>ClCCCl.ClC(OC(Cl)C)=O>[F:26][C:17]1[CH:18]=[CH:19][CH:20]=[C:21]([C:22]([F:24])([F:25])[F:23])[C:16]=1[CH2:15][C:14]([CH:11]1[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]1)=[O:27]

Participants

4

Reactant 1

HCID 22247960HCID 22247960, compound

Product 1

HCID 22247975HCID 22247975, compoundYield 43.4%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 5213051-Chloroethyl chloroformateSolvent

Procedure

After dissolving 136 mg of 1-(1-benzylpiperidin-4-yl)-2-[2-fluoro-6-(trifluoromethyl)phenyl]ethanone in 3 ml of 1,2-dichloroethane, 0.06 ml of 1-chloroethyl chloroformate was added and the mixture was stirred at room temperature for 5 minutes and then heated to reflux for 45 minutes. The solvent was distilled off under reduced pressure, 10 ml of methanol was added to the residue and heating to reflux was continued for 30 minutes. The solvent was distilled off under reduced pressure, ammonia water was added to the residue and extraction was performed with dichloromethane. After drying over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure. The residue was purified by NH silica gel column chromatography (solvent: ethyl acetate/methanol) to obtain the title compound (45 mg, 43% yield).

Workup

  1. additionwas added
  2. temperatureheated
  3. temperatureto reflux for 45 minutes
  4. distillationThe solvent was distilled off under reduced pressure, 10 ml of methanol
  5. additionwas added to the residue
  6. temperatureheating
  7. temperatureto reflux
  8. waitwas continued for 30 minutes
  9. distillationThe solvent was distilled off under reduced pressure, ammonia water
  10. additionwas added to the residue and extraction
  11. dry with materialAfter drying over anhydrous magnesium sulfate
  12. distillationthe solvent was distilled off under reduced pressure
  13. customThe residue was purified by NH silica gel column chromatography (solvent: ethyl acetate/methanol)

Sources & evidence

ORD record
ord-ae2eca61944645b98e206c0d6867d4b7
Source dataset
uspto-grants-2006_02
Patent number
US06995144B2

Reaction notes

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