2,2,2-Trichloroethyl chloroformate → cis-3-Phenyl-1-(2,2,2-trichloroethoxycarbonyl)-4-(4-trifluoromethylphenoxy)piperidine

HRID 1155608Notes

Reaction equation

HRID 1155608 reaction equation
[K].Cl[C:3]([O:5][CH2:6][C:7]([Cl:10])([Cl:9])[Cl:8])=[O:4].Cl.C[N:13]1[CH2:18][CH2:17][C@H:16]([O:19][C:20]2[CH:25]=[CH:24][C:23]([C:26]([F:29])([F:28])[F:27])=[CH:22][CH:21]=2)[C@H:15]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH2:14]1>C1C=CC=CC=1>[C:30]1([C@H:15]2[C@@H:16]([O:19][C:20]3[CH:21]=[CH:22][C:23]([C:26]([F:29])([F:27])[F:28])=[CH:24][CH:25]=3)[CH2:17][CH2:18][N:13]([C:3]([O:5][CH2:6][C:7]([Cl:10])([Cl:9])[Cl:8])=[O:4])[CH2:14]2)[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Participants

5

Reactant 3

HCID 870632,2,2-Trichloroethyl chloroformate2×HCID 5462222PotassiumHCID 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 carbohate 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-c3b8af19172e43a4be744e4457ed4353
Source dataset
uspto-grants-1981_11
Patent number
US04302590

Reaction notes

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