Sodium Hydroxide → trans-4-(4-Chlorophenoxy)-3-phenylpiperidine

HRID 851022Notes

Reaction equation

HRID 851022 reaction equation
[Cl:1][C:2]1[CH:25]=[CH:24][C:5]([O:6][C@@H:7]2[CH2:12][CH2:11][N:10](C(OCC)=O)[CH2:9][C@H:8]2[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH:4][CH:3]=1.[OH-].[Na+]>C(O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:6][C@@H:7]2[CH2:12][CH2:11][NH:10][CH2:9][C@H:8]2[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH:24][CH:25]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 12788454trans-4-(4-Chlorophenoxy)-1-ethoxycarbonyl-3-phenylpiperidine

Product 1

HCID 12788457trans-4-(4-Chlorophenoxy)-3-phenylpiperidine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 8.78 g of trans-4-(4-chlorophenoxy)-1-ethoxycarbonyl-3-phenylpiperidine, 64 ml of 20% aqueous NaOH solution and 125 ml of absolute ethanol is refluxed for 18 hours under nitrogen. The ethanol is then removed in vacuo and the aqueous residue is partitioned between dichloromethane and distilled water. The aqueous phase is extracted with dichloromethane, and the combined organic extracts are then washed with water, saturated aqueous NaCl solution, dried over anhydrous Na2SO4 and concentrated in vacuo to afford a solid which is recrystallized from cyclohexane to yield trans-4-(4-chlorophenoxy)-3-phenylpiperidine, mp 101.5°-103° C.

Workup

  1. temperatureis refluxed for 18 hours under nitrogen
  2. customThe ethanol is then removed in vacuo
  3. customthe aqueous residue is partitioned between dichloromethane
  4. distillationdistilled water
  5. extractionThe aqueous phase is extracted with dichloromethane
  6. washthe combined organic extracts are then washed with water, saturated aqueous NaCl solution
  7. dry with materialdried over anhydrous Na2SO4
  8. concentrationconcentrated in vacuo
  9. customto afford a solid which
  10. customis recrystallized from cyclohexane

Sources & evidence

ORD record
ord-1be9c11350aa46cbb183e98bd7f8b806
Source dataset
uspto-grants-1983_05
Patent number
US04382141

Reaction notes

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