Chloroform → Ethyl 4-[2-(3-methylphenyl)-2-oxoethyl]-1-piperidinecarboxylate

HRID 126863Notes

Reaction equation

HRID 126863 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([C:8](=[O:23])[CH2:9][CH:10]2[CH2:15][CH2:14][N:13](CC3C=CC=CC=3)[CH2:12][CH2:11]2)[CH:5]=[CH:6][CH:7]=1.C(=O)([O-])[O-].[Na+].[Na+].ClC(Cl)Cl.Cl[C:35]([O:37][CH2:38][CH3:39])=[O:36]>O>[CH3:1][C:2]1[CH:3]=[C:4]([C:8](=[O:23])[CH2:9][CH:10]2[CH2:11][CH2:12][N:13]([C:35]([O:37][CH2:38][CH3:39])=[O:36])[CH2:14][CH2:15]2)[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 6212ChloroformHCID 10340Sodium CarbonateHCID 10928Ethyl chloroformateHCID 202880471-(3-Methylphenyl)-2-[1-(phenylmethyl)-4-piperidinyl]ethanone

Product 1

HCID 20288050Ethyl 4-[2-(3-methylphenyl)-2-oxoethyl]-1-piperidinecarboxylateYield 91%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred mixture of 20.9 parts of 1-(3-methylphenyl)-2-[1-(phenylmethyl)-4-piperidinyl]ethanone, 0.75 parts of sodium carbonate and 150 parts of trichloromethane are added dropwise 8.1 parts of ethyl chloroformate. Upon completion, stirring is continued overnight at room temperature. Water is added to the reaction mixture and the layers are separated. The aqueous phase is extracted with trichloromethane. The combined organic phases are washed with water, dried, filtered and evaporated. The residue is purified by column-chromatography over silica gel using a mixture of trichloromethane and methanol (95:5 by volume) as eluent. The pure fractions are collected and the eluent is evaporated, yielding 18 parts (91%) of ethyl 4-[2-(3-methylphenyl)-2-oxoethyl]-1-piperidinecarboxylate as an oily residue.

Workup

  1. customthe layers are separated
  2. extractionThe aqueous phase is extracted with trichloromethane
  3. washThe combined organic phases are washed with water
  4. customdried
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue is purified by column-chromatography over silica gel using
  8. additiona mixture of trichloromethane and methanol (95:5 by volume) as eluent
  9. customThe pure fractions are collected
  10. customthe eluent is evaporated

Sources & evidence

ORD record
ord-e00cb53976ae4c9ea04bb7d19aeff99b
Source dataset
uspto-grants-1981_03
Patent number
US04254127

Reaction notes

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