Sodium Sulfate → HCID 86738223, compound

HRID 851046Notes

Reaction equation

HRID 851046 reaction equation
C(O[C:4]([N:6]1[CH2:11][CH2:10][C@H:9]([O:12][C:13]2[CH:18]=[CH:17][C:16]([CH3:19])=[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.[H-].[Al+3].[Li+].[H-].[H-].[H-].S([O-])([O-])(=O)=O.[Na+].[Na+].[C:39]([OH:46])(=[O:45])/[CH:40]=[CH:41]/[C:42]([OH:44])=[O:43]>O1CCCC1.CCOCC.C(O)C>[C:39]([OH:46])(=[O:45])/[CH:40]=[CH:41]/[C:42]([OH:44])=[O:43].[CH3:4][N:6]1[CH2:11][CH2:10][C@H:9]([O:12][C:13]2[CH:18]=[CH:17][C:16]([CH3:19])=[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

Participants

8

Reactant 4

HCID 24436Sodium SulfateHCID 444972Fumaric AcidHCID 21226445Aluminium lithium hydrideHCID 70530989HCID 70530989, compound

Product 1

HCID 86738223HCID 86738223, compound

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 3283Diethyl EtherSolvent3×HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
5 °C

Procedure

A solution of 3.12 g of cis-1-ethoxycarbonyl-3-phenyl-4-(4-tolyloxy)piperidine in 55 ml of anhydrous tetrahydrofuran is added dropwise under nitrogen to a suspension of 1.05 g of lithium aluminum hydride in 55 ml of tetrahydrofuran. The resulting mixture is refluxed for 2 hours, cooled to 5° C. and diluted with 100 ml of anhydrous ether. Saturated sodium sulfate solution is added dropwise with cooling until a flocculent white precipitate forms. The solid is filtered, washed with ether, and the filtrate is concentrated in vacuo to a colorless oil. The oil is dissolved in 150 ml of ether, washed with 100 ml of saturated sodium chloride solution, dried over anhydrous sodium sulfate, and concentrated in vacuo to afford a colorless oil. This oil is dissolved in ether (100 ml) and treated dropwise with a solution of 1.12 g of fumaric acid in a mixture of ether (100 ml) and ethanol (25 ml). The solvent is removed in vacuo, and the residue is triturated into solid with ether. The crystalline solid is filtered, washed with ether and dried. The filtrate is concentrated in vacuo to an oil and 1 ml of ethanol is added followed by approximately 5 ml of ether. The solution is seeded with the crystalline solid and another 5 ml of ether is slowly added. The solution is scratched to afford a second crop of salt. The two crops are combined and recrystallized by dissolving in 100 ml of boiling ethyl acetate, filtering the solution hot and boiling the filtrate down to a volume of 50 ml. The solid is filtered, washed with ethyl acetate and ether and dried to afford product as colorless crystals, mp 148°-150° C.

Workup

  1. temperatureThe resulting mixture is refluxed for 2 hours
  2. temperaturewith cooling until a flocculent white precipitate forms
  3. filtrationThe solid is filtered
  4. washwashed with ether
  5. concentrationthe filtrate is concentrated in vacuo to a colorless oil
  6. dissolutionThe oil is dissolved in 150 ml of ether
  7. washwashed with 100 ml of saturated sodium chloride solution
  8. dry with materialdried over anhydrous sodium sulfate
  9. concentrationconcentrated in vacuo
  10. customto afford a colorless oil
  11. customThe solvent is removed in vacuo
  12. customthe residue is triturated into solid with ether
  13. filtrationThe crystalline solid is filtered
  14. washwashed with ether
  15. customdried
  16. concentrationThe filtrate is concentrated in vacuo to an oil and 1 ml of ethanol
  17. additionis added
  18. additionanother 5 ml of ether is slowly added
  19. customto afford a second crop of salt
  20. customrecrystallized
  21. dissolutionby dissolving in 100 ml of boiling ethyl acetate
  22. filtrationfiltering the solution hot
  23. filtrationThe solid is filtered
  24. washwashed with ethyl acetate and ether
  25. customdried
  26. customto afford product as colorless crystals, mp 148°-150° C.

Sources & evidence

ORD record
ord-61838df5468d4aef9243ab908183c2fb
Source dataset
uspto-grants-1983_05
Patent number
US04382141

Reaction notes

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