Sodium Sulfate → HCID 86738227, compound

HRID 1106344Notes

Reaction equation

HRID 1106344 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].C(O[C:10]([N:12]1[CH2:17][CH2:16][C@H:15]([O:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[F:25])[C@H:14]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH2:13]1)=O)C.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].[F:25][C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=1[O:18][C@H:15]1[CH2:16][CH2:17][N:12]([CH3:10])[CH2:13][C@H:14]1[C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1

Participants

8

Reactant 4

HCID 24436Sodium SulfateHCID 444972Fumaric AcidHCID 21226445Aluminium lithium hydrideHCID 70533094HCID 70533094, compound

Product 1

HCID 86738227HCID 86738227, compound

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 3283Diethyl EtherSolvent3×HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To a suspension of 1.82 g of lithium aluminum hydride in 100 ml of anhydrous tetrahydrofuran is added a solution of 5.51 g of cis-1-ethoxycarbonyl-4-(2-fluorophenoxy)-3-phenylpiperidine in 100 ml of tetrahydrofuran. The mixture is refluxed for 2 hours under nitrogen, cooled to 0° C. and diluted with ether (100 ml). Saturated sodium sulfate solution is cautiously added dropwise at 0°-10° C. until a flocculent white precipitate is obtained. The solid is filtered, washed with ether and the filtrate is concentrated in vacuo. The residue is taken up in ether (200 ml), the solution is washed with saturated sodium chloride and dried over anhydrous sodium sulfate. Filtration and concentration in vacuo affords a nearly colorless oil. The oil is dissolved in 100 ml of ether and treated dropwise with a solution of 1.92 g of fumaric acid in a mixture of ether (150 ml) and absolute ethanol (25 ml). After stirring overnight the precipitated solid is filtered, washed with ether and dried to afford a colorless solid. Recrystallization from 25 ml of isopropanol gives product as colorless crystals, mp 148°-151° C.

Workup

  1. temperatureThe mixture is refluxed for 2 hours under nitrogen
  2. customis obtained
  3. filtrationThe solid is filtered
  4. washwashed with ether
  5. concentrationthe filtrate is concentrated in vacuo
  6. washthe solution is washed with saturated sodium chloride
  7. dry with materialdried over anhydrous sodium sulfate
  8. filtrationFiltration and concentration in vacuo
  9. customaffords a nearly colorless oil
  10. filtrationis filtered
  11. washwashed with ether
  12. customdried
  13. customto afford a colorless solid
  14. customRecrystallization from 25 ml of isopropanol
  15. customgives product as colorless crystals, mp 148°-151° C.

Sources & evidence

ORD record
ord-083f02a3df78424b80276079e462ab0c
Source dataset
uspto-grants-1982_01
Patent number
US04312876

Reaction notes

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