Potassium Carbonate → cis-3-Phenyl-1-(2,2,2-trichloroethoxycarbonyl)-4-(4-trifluoromethylphenoxy)piperidine

HRID 1106311Notes

Reaction equation

HRID 1106311 reaction equation
C(=O)([O-])[O-].[K+].[K+].Cl[C:8]([O:10][CH2:11][C:12]([Cl:15])([Cl:14])[Cl:13])=[O:9].Cl.C[N:18]1[CH2:23][CH2:22][C@H:21]([O:24][C:25]2[CH:30]=[CH:29][C:28]([C:31]([F:34])([F:33])[F:32])=[CH:27][CH:26]=2)[C@H:20]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[CH2:19]1>C1C=CC=CC=1>[C:35]1([C@H:20]2[C@@H:21]([O:24][C:25]3[CH:26]=[CH:27][C:28]([C:31]([F:34])([F:32])[F:33])=[CH:29][CH:30]=3)[CH2:22][CH2:23][N:18]([C:8]([O:10][CH2:11][C:12]([Cl:15])([Cl:14])[Cl:13])=[O:9])[CH2:19]2)[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 870632,2,2-Trichloroethyl chloroformate2×HCID 12788392cis-1-Methyl-3-phenyl-4-(4-trifluoromethylphenoxy)piperidine hydrochloride

Product 1

HCID 86737139cis-3-Phenyl-1-(2,2,2-trichloroethoxycarbonyl)-4-(4-trifluoromethylphenoxy)piperidine

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

0.46 g of anhydrous potassium carbonate and 0.5 ml of 2,2,2-trichloroethyl chloroformate are added under nitrogen to a solution of 1.11 g of the free base of cis-1-methyl-3-phenyl-4-(4-trifluoromethylphenoxy)piperidine of Example 22 in 10 ml of dry benzene. After 1 hour at room temperature the mixture is refluxed 18 hours. Another 0.045 ml of 2,2,2-trichloroethyl chloroformate is added, the mixture is again refluxed 18 hours, then cooled and partitioned between ether and water. The organic phase is washed with saturated aqueous NaCl solution, dried over anhydrous Na2SO4, and concentrated in vacuo to an oil. This material is dissolved in benzene and filtered through a column of silica gel, then is further purified by preparative chromatography on five 2 mm silica preparative plates, using 3:1 petroleum ether as solvent. A nearly colorless glass of cis-3-phenyl-1-(2,2,2-trichloroethoxycarbonyl)-4-(4-trifluoromethylphenoxy)piperidine is obtained.

Workup

  1. temperaturecooled
  2. custompartitioned between ether and water
  3. washThe organic phase is washed with saturated aqueous NaCl solution
  4. dry with materialdried over anhydrous Na2SO4
  5. concentrationconcentrated in vacuo to an oil
  6. dissolutionThis material is dissolved in benzene
  7. filtrationfiltered through a column of silica gel
  8. customis further purified by preparative chromatography on five 2 mm silica preparative plates

Sources & evidence

ORD record
ord-2d09d640f70340b8824af53cb621b881
Source dataset
uspto-grants-1982_01
Patent number
US04312876

Reaction notes

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