Sodium Acetate → Oxalic acid--4-(1-benzylpiperidin-3-yl)-1,2-phenylene diacetate (1/1)

HRID 616034Notes

Reaction equation

HRID 616034 reaction equation
[C:1]([O-:4])(=[O:3])[CH3:2].[Na+].[C:6]([OH:11])(=[O:10])[C:7]([OH:9])=[O:8].[CH2:12]([N:19]1[CH2:24][CH2:23][CH2:22][CH:21]([C:25]2[CH:30]=[CH:29][C:28](O)=[C:27]([OH:32])[CH:26]=2)[CH2:20]1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>C(OC(=O)C)(=O)C>[C:6]([OH:11])(=[O:10])[C:7]([OH:9])=[O:8].[CH2:12]([N:19]1[CH2:24][CH2:23][CH2:22][CH:21]([C:25]2[CH:30]=[CH:29][C:28]([O:3][C:1](=[O:4])[CH3:2])=[C:27]([O:32][C:7](=[O:8])[CH3:6])[CH:26]=2)[CH2:20]1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 517045Sodium AcetateHCID 20370845HCID 20370845, compound

Product 1

HCID 3046215Oxalic acid--4-(1-benzylpiperidin-3-yl)-1,2-phenylene diacetate (1/1)Yield 224.9%

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Conditions

Temperature
20 °C

Procedure

9.8 g of anhydrous sodium acetate were added to a mixture of 9.8 g of N-benzyl-3-(3',4'-dihydroxyphenyl)-piperidine oxalate and 120 ml of acetic acid anhydride and the mixture was stirred for 3 hours at 20° C and was filtered. The filter was washed with ethanol and the filtrate was evaporated to dryness under reduced pressure. The residue was taken up in water and ethyl acetate and the solution was made alkaline with an aqueous solution saturated with sodium bicarbonate. The organic phase was decanted, dried and evaporated to dryness. The residue was dissolved in 50 ml of isopropanol and a solution of 4 g of oxalic acid in 30 ml of isopropanol was added thereto. The mixture was refluxed until dissolution occurred and after cooling to 20° C, the mixture was vacuum filtered to obtain 13.5 g of N-benzyl-3-(3',4'-diacetoxyphenyl)-piperidine oxalate melting at 145° C.

Workup

  1. filtrationwas filtered
  2. washThe filter was washed with ethanol
  3. customthe filtrate was evaporated to dryness under reduced pressure
  4. customThe organic phase was decanted
  5. customdried
  6. customevaporated to dryness
  7. dissolutionThe residue was dissolved in 50 ml of isopropanol
  8. additiona solution of 4 g of oxalic acid in 30 ml of isopropanol was added
  9. temperatureThe mixture was refluxed until dissolution
  10. temperatureafter cooling to 20° C
  11. filtrationfiltered

Sources & evidence

ORD record
ord-faaa93b49d4a453aa7e78ffcbe461d86
Source dataset
uspto-grants-1978_02
Patent number
US04072685

Reaction notes

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