1,2-Dichloroethane → 2-(2-Fluorophenyl)-1-(piperidin-4-yl)ethanone hydrochloride

HRID 890027Notes

Reaction equation

HRID 890027 reaction equation
C([N:8]1[CH2:13][CH2:12][CH:11]([C:14](=[O:23])[CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[F:22])[CH2:10][CH2:9]1)C1C=CC=CC=1.[Cl:24]CCCl>ClC(OC(Cl)C)=O>[ClH:24].[F:22][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=1[CH2:15][C:14]([CH:11]1[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]1)=[O:23]

Participants

4

Reactant 2

HCID 111,2-DichloroethaneHCID 222479931-(1-Benzylpiperidin-4-yl)-2-(2-fluorophenyl)ethanone

Product 1

HCID 222481242-(2-Fluorophenyl)-1-(piperidin-4-yl)ethanone hydrochlorideYield 92%

Reagents, catalysts & solvents 1

HCID 5213051-Chloroethyl chloroformateSolvent

Procedure

After dissolving 1.27 g of 1-(1-benzylpiperidin-4-yl)-2-(2-fluorophenyl)ethanone in 8 ml of 1,2-dichloroethane, 0.53 ml of 1-chloroethyl chloroformate was added while stirring on ice, and the mixture was heated to reflux for 1 hour. The solvent was distilled off under reduced pressure, 8 ml of methanol was added to the residue, and heating to reflux was continued for 40 minutes. The solvent was distilled off under reduced pressure, ethyl acetate was added to the residue, and the precipitate was filtered out to obtain the title compound (970 mg, 92% 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, 8 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
  9. additionwas added to the residue
  10. filtrationthe precipitate was filtered out

Sources & evidence

ORD record
ord-90d6f9cbc5ce46b78e3bf3373bca84a1
Source dataset
uspto-grants-2006_02
Patent number
US06995144B2

Reaction notes

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