Ethyl chloroformate → trans-4-(4-Chlorophenoxy)-1-ethoxycarbonyl-3-phenylpiperidine

HRID 851021Notes

Reaction equation

HRID 851021 reaction equation
[Cl:1][C:2]1[CH:21]=[CH:20][C:5]([O:6][C@@H:7]2[CH2:12][CH2:11][N:10](C)[CH2:9][C@H:8]2[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Cl[C:29]([O:31][CH2:32][CH3:33])=[O:30]>C1C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:6][C@@H:7]2[CH2:12][CH2:11][N:10]([C:29]([O:31][CH2:32][CH3:33])=[O:30])[CH2:9][C@H:8]2[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:20][CH:21]=1

Participants

5

Reactant 3

HCID 10928Ethyl chloroformateHCID 11430Potassium CarbonateHCID 12788446trans-4-(4-Chlorophenoxy)-1-methyl-3-phenylpiperidine

Product 1

HCID 12788454trans-4-(4-Chlorophenoxy)-1-ethoxycarbonyl-3-phenylpiperidine

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of 10.26 g of trans-4-(4-chlorophenoxy)-1-methyl-3-phenylpiperidine of Example 26, 7.05 g of anhydrous potassium carbonate, 75 ml of dry benzene and 5.53 g of ethyl chloroformate is refluxed for 18 hours under nitrogen. The mixture is then partitioned between distilled water and hexane. The organic phase is washed with water, the combined aqueous extracts are extracted with hexane, the combined organic extracts are washed with saturated aqueous NaCl solution, dried over anhydrous MgSO4, and concentrated in vacuo to afford an oil which almost completely crystallizes after standing for about 64 hours. The colorless solid is triturated with hexane, filtered and washed well with hexane to afford trans-4-(4-chlorophenoxy)-1-ethoxycarbonyl-3-phenylpiperidine, m.p. s 80°, 81.5°-84° C.

Workup

  1. temperatureis refluxed for 18 hours under nitrogen
  2. customThe mixture is then partitioned
  3. distillationbetween distilled water and hexane
  4. washThe organic phase is washed with water
  5. extractionthe combined aqueous extracts are extracted with hexane
  6. washthe combined organic extracts are washed with saturated aqueous NaCl solution
  7. dry with materialdried over anhydrous MgSO4
  8. concentrationconcentrated in vacuo
  9. customto afford an oil which
  10. customalmost completely crystallizes
  11. customThe colorless solid is triturated with hexane
  12. filtrationfiltered
  13. washwashed well with hexane

Sources & evidence

ORD record
ord-c30e6659b2d14011a2c999ff8b878900
Source dataset
uspto-grants-1983_05
Patent number
US04382141

Reaction notes

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