Potassium Carbonate → HCID 70513622, compound

HRID 851035Notes

Reaction equation

HRID 851035 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:19]=[CH:20][CH:21]=1)[O:5][C@H:6]1[CH2:11][CH2:10][N:9](C)[CH2:8][C@H:7]1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(=O)([O-])[O-].[K+].[K+].Cl[C:29]([O:31][CH2:32][C:33]([Cl:36])([Cl:35])[Cl:34])=[O:30].ClC([O-])=O>C1C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]([CH:19]=[CH:20][CH:21]=1)[O:5][C@H:6]1[CH2:11][CH2:10][N:9]([C:29]([O:31][CH2:32][C:33]([Cl:36])([Cl:35])[Cl:34])=[O:30])[CH2:8][C@H:7]1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 870632,2,2-Trichloroethyl chloroformateHCID 12788471HCID 12788471, compoundHCID 21226386Carbonochloridate

Product 1

HCID 70513622HCID 70513622, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of 2.48 g of the free base cis-4-(3-chlorophenoxy)-1-methyl-3-phenylpiperidine, of Example 36, 1.14 g of anhydrous potassium carbonate and 30 ml of dry benzene is treated with 1.42 ml of 2,2,2-trichloroethyl chloroformate. After 30 minutes at room temperature the mixture is refluxed 18 hours. Another 0.36 ml of chloroformate is added, and the mixture is refluxed another 4 hours. The mixture is then cooled and partitioned between 100 ml of ether and 50 ml of water. The aqueous phase is extracted with 50 ml of ether, and the combined organic extracts are washed with 2 N HCl solution, saturated aqueous NaCl solution, and dried over Na2SO4. Concentration in vacuo affords a mixture of a solid and an oil which is triturated with 25 ml of ether and then diluted with hexane to a volume of about 125 ml. After refrigeration for 18 hours the mixture is filtered, the solid is washed with hexane, and the filtrate is washed successively with 10% aqueous NaOH solution, water, and saturated aqueous NaCl solution. After drying over Na2SO4 the solution is concentrated in vacuo to a gum. Chromatography of this material on silica gel affords a colorless gum of cis-4-(3-chlorophenoxy)-3-phenyl-1-(2,2,2-trichloroethoxycabonyl) piperidine.

Workup

  1. temperaturethe mixture is refluxed another 4 hours
  2. temperatureThe mixture is then cooled
  3. custompartitioned between 100 ml of ether and 50 ml of water
  4. extractionThe aqueous phase is extracted with 50 ml of ether
  5. washthe combined organic extracts are washed with 2 N HCl solution, saturated aqueous NaCl solution
  6. dry with materialdried over Na2SO4
  7. concentrationConcentration in vacuo
  8. customaffords
  9. additiona mixture of a solid
  10. customan oil which is triturated with 25 ml of ether
  11. additiondiluted with hexane to a volume of about 125 ml
  12. filtrationAfter refrigeration for 18 hours the mixture is filtered
  13. washthe solid is washed with hexane
  14. washthe filtrate is washed successively with 10% aqueous NaOH solution, water, and saturated aqueous NaCl solution
  15. dry with materialAfter drying over Na2SO4 the solution
  16. concentrationis concentrated in vacuo to a gum

Sources & evidence

ORD record
ord-9baddcf1ebe94c189f490a2cbb41938f
Source dataset
uspto-grants-1983_05
Patent number
US04382141

Reaction notes

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