Potassium Carbonate → HCID 86738224, compound

HRID 851048Notes

Reaction equation

HRID 851048 reaction equation
[F:1][C:2]1[CH:20]=[CH:19][C:5]([O:6][C@@H:7]2[CH2:12][CH2:11][NH:10][CH2:9][C@H:8]2[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:28][CH:29]=[C:30]([CH3:32])[CH3:31].[C:33]([OH:40])(=[O:39])/[CH:34]=[CH:35]/[C:36]([OH:38])=[O:37]>CCOCC.C(O)C.CN(C)C=O>[C:33]([OH:40])(=[O:39])/[CH:34]=[CH:35]/[C:36]([OH:38])=[O:37].[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:6][C@@H:7]2[CH2:12][CH2:11][N:10]([CH2:28][CH:29]=[C:30]([CH3:32])[CH3:31])[CH2:9][C@H:8]2[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:19][CH:20]=1

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 700922-Butene, 1-bromo-3-methyl-HCID 444972Fumaric AcidHCID 12788502HCID 12788502, compound

Product 1

HCID 86738224HCID 86738224, compound

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 3283Diethyl EtherSolvent2×HCID 6228DimethylformamideSolvent

Conditions

Temperature
79 °C

Procedure

A mixture of 4.34 g trans-4-(4-fluorophenoxy)-3-phenylpiperidine, 4.8 g of anhydrous potassium carbonate, 2.62 g of 1-bromo-3-methyl-2-butene and 64 ml of dry dimethylformamide is heated and vigorously stirred overnight at 79° C. under nitrogen. The mixture is cooled to room temperature and partitioned between water (300 ml) and ether (500 ml). The phases are separated and the ether phase is washed with water (3×300 ml), followed by 300 ml of saturated sodium chloride solution. After drying over anhydrous sodium sulfate the ether extracts are filtered and concentrated in vacuo to a brown oil which crystallized upon standing. The crystalline solid is dissolved in 50 ml of boiling hexane and filtered to remove a dark brown gummy residue. Evaporation of the solvent in vacuo afforded an oil which crystallized under high vacuum to afford a dark orange solid. The solid is dissolved in ether (50 ml) and treated dropwise with a solution of 1.53 g of fumaric acid in a mixture of 100 ml of ether and 25 ml of absolute ethanol. The crude salt is filtered, washed with ether, dried and recrystallized from 325 ml of isopropanol to give product as colorless, fluffy platelets, mp 215°-217° C. dec.

Workup

  1. temperatureThe mixture is cooled to room temperature
  2. custompartitioned between water (300 ml) and ether (500 ml)
  3. customThe phases are separated
  4. washthe ether phase is washed with water (3×300 ml)
  5. dry with materialAfter drying over anhydrous sodium sulfate the ether extracts
  6. filtrationare filtered
  7. concentrationconcentrated in vacuo to a brown oil which
  8. customcrystallized
  9. dissolutionThe crystalline solid is dissolved in 50 ml of boiling hexane
  10. filtrationfiltered
  11. customto remove a dark brown gummy residue
  12. customEvaporation of the solvent in vacuo
  13. customafforded an oil which
  14. customcrystallized under high vacuum
  15. customto afford a dark orange solid
  16. filtrationThe crude salt is filtered
  17. washwashed with ether
  18. customdried
  19. customrecrystallized from 325 ml of isopropanol
  20. customto give product as colorless, fluffy platelets, mp 215°-217° C. dec.

Sources & evidence

ORD record
ord-993a75ea3c274a869e790bb58148dc65
Source dataset
uspto-grants-1983_05
Patent number
US04382141

Reaction notes

Loading…