1,2-Dichloroethane → 1-(Piperidin-4-yl)-2-[2-(trifluoromethyl)phenyl)ethanone hydrochloride

HRID 914833Notes

Reaction equation

HRID 914833 reaction equation
C([N:8]1[CH2:13][CH2:12][CH:11]([C:14](=[O:26])[CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[C:22]([F:25])([F:24])[F:23])[CH2:10][CH2:9]1)C1C=CC=CC=1.[Cl:27]CCCl>ClC(OC(Cl)C)=O>[ClH:27].[NH:8]1[CH2:9][CH2:10][CH:11]([C:14](=[O:26])[CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[C:22]([F:24])([F:25])[F:23])[CH2:12][CH2:13]1

Participants

4

Reactant 2

HCID 111,2-DichloroethaneHCID 222479231-(1-Benzylpiperidin-4-yl)-2-[2-(trifluoromethyl)phenyl]ethanone

Product 1

HCID 222484771-(Piperidin-4-yl)-2-[2-(trifluoromethyl)phenyl)ethanone hydrochlorideYield 83%

Reagents, catalysts & solvents 1

HCID 5213051-Chloroethyl chloroformateSolvent

Procedure

After dissolving 1.30 g of 1-(1-benzylpiperidin-4-yl)-2-[2-(trifluoromethyl)phenyl]ethanone in 10 ml of 1,2-dichloroethane, 0.58 ml of 1-chloroethyl chloroformate was added while stirring at room temperature and the mixture was heated to reflux for 1 hour. 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, ethyl acetate/n-hexane was added to the residue and the precipitate was filtered out to obtain the title compound (916 mg, 83% yield).

Workup

  1. additionwas added
  2. temperaturethe mixture was heated
  3. temperatureto reflux for 1 hour
  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. distillationThe solvent was distilled off under reduced pressure, ethyl acetate/n-hexane
  9. additionwas added to the residue
  10. filtrationthe precipitate was filtered out

Sources & evidence

ORD record
ord-0fe93a217a3a4c24b909daae5c0c5745
Source dataset
uspto-grants-2007_09
Patent number
US07265108B2

Reaction notes

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