Sodium Hydroxide → HCID 12788504, compound

HRID 2295454Notes

Reaction equation

HRID 2295454 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.[OH-].[Na+].[C:28]([OH:35])(=[O:34])/[CH:29]=[CH:30]/[C:31]([OH:33])=[O:32]>CCOCC.C(O)C>[C:28]([OH:35])(=[O:34])/[CH:29]=[CH:30]/[C:31]([OH:33])=[O:32].[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

6

Reactant 3

HCID 14798Sodium HydroxideHCID 444972Fumaric AcidHCID 12788499HCID 12788499, compound

Product 1

HCID 12788504HCID 12788504, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 3283Diethyl EtherSolvent2×

Procedure

A mixture of 3.44 g of trans-1-ethoxycarbonyl-4-(4-fluorophenoxy)-3-phenylpiperidine of Example 47, 50 ml of absolute ethanol and 26 ml of 20% aqueous NaOH solution is refluxed 18 hours under a nitrogen atmosphere. The ethanol is removed in vacuo, and the aqueous residue is partitioned between water and ethyl acetate. The aqueous phase is extracted with ethyl acetate, and the combined organic extracts are washed with saturated aqueous NaCl solution, dried over anhydrous Na2SO4, and concentrated in vacuo to an oil which quickly crystallizes to a solid. The solid is triturated with hexane and filtered to afford a solid, m.p. 99°-101° C. This material is dissolved in 100 ml of ether and treated dropwise with a solution of 1.05 g of fumaric acid in a mixture of 60 ml of ether and 15 ml of absolute ethanol. The resultant solid is filtered, washed with ether and dried to afford a salt of trans-4-(4-fluorophenoxy)-3-phenylpiperidine fumarate, m.p. s 142.5°, 143° C. dec.

Workup

  1. temperatureis refluxed 18 hours under a nitrogen atmosphere
  2. customThe ethanol is removed in vacuo
  3. customthe aqueous residue is partitioned between water and ethyl acetate
  4. extractionThe aqueous phase is extracted with ethyl acetate
  5. washthe combined organic extracts are washed with saturated aqueous NaCl solution
  6. dry with materialdried over anhydrous Na2SO4
  7. concentrationconcentrated in vacuo to an oil which
  8. customquickly crystallizes to a solid
  9. customThe solid is triturated with hexane
  10. filtrationfiltered
  11. customto afford a solid, m.p. 99°-101° C
  12. filtrationThe resultant solid is filtered
  13. washwashed with ether
  14. customdried

Sources & evidence

ORD record
ord-1f7bc4b79ac042ca9ea1921cf18fcad4
Source dataset
uspto-grants-1984_01
Patent number
US04424357

Reaction notes

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