Sodium Hydroxide → HCID 12788532, compound

HRID 851027Notes

Reaction equation

HRID 851027 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:23]=[CH:24][CH:25]=1)[O:5][C@@H:6]1[CH2:11][CH2:10][N:9](C(OCC)=O)[CH2:8][C@H:7]1[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[OH-].[Na+]>C(O)C>[ClH:1].[Cl:1][C:2]1[CH:3]=[C:4]([CH:23]=[CH:24][CH:25]=1)[O:5][C@@H:6]1[CH2:11][CH2:10][NH:9][CH2:8][C@H:7]1[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 70514099HCID 70514099, compound

Product 1

HCID 12788532HCID 12788532, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 3.84 g of trans-4-(3-chlorophenoxy)-1-ethoxycarbonyl-3-phenylpiperidine of Example 33, 55 ml of absolute ethanol, and 28 ml of 10% aqueous NaOH solution is refluxed for 18 hours under nitrogen. The ethanol is then removed in vacuo and the aqueous residue is extracted with ether. The combined ether extracts are washed with saturated aqueous NaCl solution, dried over anhydrous MgSO4, and concentrated in vacuo to an oil. This oil is dissolved in ether, filtered, and the filtrate treated with HCl-saturated ether solution until acidic to wet pH paper. The resulting precipitate is filtered, washed with ether and dried to afford a solid, m.p. 239°-241° C. Recrystallization from isopropanol affords crystals of trans-4-(3-chlorophenoxy)-3-phenylpiperidine hydrochloride, mp s 240°, 241.5°-243.5° C.

Workup

  1. temperatureis refluxed for 18 hours under nitrogen
  2. customThe ethanol is then removed in vacuo
  3. extractionthe aqueous residue is extracted with ether
  4. washThe combined ether extracts are washed with saturated aqueous NaCl solution
  5. dry with materialdried over anhydrous MgSO4
  6. concentrationconcentrated in vacuo to an oil
  7. dissolutionThis oil is dissolved in ether
  8. filtrationfiltered
  9. additionthe filtrate treated with HCl-saturated ether solution until acidic to wet pH paper
  10. filtrationThe resulting precipitate is filtered
  11. washwashed with ether
  12. customdried
  13. customto afford a solid, m.p. 239°-241° C
  14. customRecrystallization from isopropanol

Sources & evidence

ORD record
ord-1e54037010c042ddb212a420b7e586fb
Source dataset
uspto-grants-1983_05
Patent number
US04382141

Reaction notes

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