Hydrochloric Acid → HCID 70531338, compound

HRID 1106338Notes

Reaction equation

HRID 1106338 reaction equation
C(OC([N:6]1[CH2:11][CH2:10][C@H:9]([O:12][C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=2)[C@H:8]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:7]1)=O)C.C(O)C.[OH-].[Na+].[ClH:31]>CCOCC.C(OCC)(=O)C>[ClH:31].[F:19][C:16]1[CH:15]=[CH:14][C:13]([O:12][C@H:9]2[CH2:10][CH2:11][NH:6][CH2:7][C@H:8]2[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[CH:18][CH:17]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 14798Sodium HydroxideHCID 12788500HCID 12788500, compound

Product 1

HCID 70531338HCID 70531338, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 3.62 g of cis-1-ethoxycarbonyl-4-(4-fluorophenoxy)-3-phenylpiperidine, 52 ml of absolute ethanol and 28 ml of 20% sodium hydroxide solution is refluxed overnight under nitrogen. The ethanol is then removed in vacuo and the aqueous residue partitioned between water (50 ml) and ether (100 ml). The phases are separated and the aqueous phase extracted with 2×100 ml of ether. The combined ether extracts are washed with 100 ml of saturated sodium chloride solution and dried overnight over anhydrous sodium sulfate. Filtration and concentration in vacuo affords a cloudy yellow oil. The oil is dissolved in ether and treated dropwise with saturated ethereal hydrogen chloride. The solvent is removed in vacuo and the resulting foam triturated with ether to afford a nearly colorless solid. The solid is dissolved in 70 ml of boiling ethyl acetate, filtered hot, and the filtrate concentrated to a volume of 30 ml. The solution is scratched, seeded and allowed to stand overnight at room temperature. Filtration followed by washing with ethyl acetate and ether and drying in vacuo affords the product as a colorless crystalline solid, mp 150°-152° C.

Workup

  1. temperatureis refluxed overnight under nitrogen
  2. customThe ethanol is then removed in vacuo
  3. customthe aqueous residue partitioned between water (50 ml) and ether (100 ml)
  4. customThe phases are separated
  5. extractionthe aqueous phase extracted with 2×100 ml of ether
  6. washThe combined ether extracts are washed with 100 ml of saturated sodium chloride solution
  7. dry with materialdried overnight over anhydrous sodium sulfate
  8. filtrationFiltration and concentration in vacuo
  9. customaffords a cloudy yellow oil
  10. customThe solvent is removed in vacuo
  11. customthe resulting foam triturated with ether
  12. customto afford a nearly colorless solid
  13. filtrationfiltered hot
  14. concentrationthe filtrate concentrated to a volume of 30 ml
  15. filtrationFiltration
  16. washby washing with ethyl acetate and ether
  17. customdrying in vacuo

Sources & evidence

ORD record
ord-30828220e06542049b96d7cde49a3954
Source dataset
uspto-grants-1982_01
Patent number
US04312876

Reaction notes

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