Carbon Dioxide → HCID 54227188, compound

HRID 1390356Notes

Reaction equation

HRID 1390356 reaction equation
[CH2:1]([O:3][C:4]([N:6]1[CH2:11][C@H:10]([CH3:12])[NH:9][C@H:8]([CH3:13])[CH2:7]1)=[O:5])[CH3:2].[C:14]1(C)[CH:19]=CC(S(OCCC)(=O)=O)=C[CH:15]=1.C(=O)([O-])[O-].[Na+].[Na+].C(=O)=O>C(O)C>[CH2:1]([O:3][C:4]([N:6]1[CH2:7][C@@H:8]([CH3:13])[N:9]([CH2:15][CH2:14][CH3:19])[C@@H:10]([CH3:12])[CH2:11]1)=[O:5])[CH3:2]

Participants

6

Reactant 4

HCID 280Carbon DioxideHCID 10340Sodium CarbonateHCID 69035Propyl p-toluenesulfonateHCID 543631961-Ethoxycarbonyl-cis-3,5-dimethylpiperazine

Product 1

HCID 54227188HCID 54227188, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 25.8 grams of 1-ethoxycarbonyl-cis-3,5-dimethylpiperazine, 38.6 grams of propyl 4-toluene-sulfonate, 90 ml. of absolute ethanol and 9.5 grams of sodium carbonate is stirred and heated to reflux. After 30 minutes of reflux, vigorous evolution of carbon dioxide begins and continues for about 5 hours. Refluxing is continued for a total of 22 hours. The reaction mixture is then cooled and filtered and the solvent is evaporated. The resulting residue is mixed with 300 ml. of aqueous 1 N sodium hydroxide solution and the mixture is extracted with ethyl ether. The ether extract is washed successively with 100 ml. of aqueous 1 N sodium hydroxide and 100 ml. of water and then dried over anhydrous sodium sulfate. The organic solution is then treated with charcoal and the solvent is evaporated to leave a residue which is purified by chromatography to give 4-ethoxycarbonyl-cis-2,6-dimethyl-1-propylpiperazine. If 1-ethoxycarbonyl-cis-2,6-dimethylpiperazine is reacted with propyl 4-toluenesulfonate according to this same procedure, the product obtained is 1-ethoxycarbonyl-cis-2,6-dimethyl-4-propylpiperazine.

Workup

  1. temperatureheated to reflux
  2. temperatureAfter 30 minutes of reflux
  3. temperatureRefluxing
  4. customis continued for a total of 22 hours
  5. temperatureThe reaction mixture is then cooled
  6. filtrationfiltered
  7. customthe solvent is evaporated
  8. additionThe resulting residue is mixed with 300 ml
  9. extractionof aqueous 1 N sodium hydroxide solution and the mixture is extracted with ethyl ether
  10. extractionThe ether extract
  11. washis washed successively with 100 ml
  12. dry with materialof water and then dried over anhydrous sodium sulfate
  13. additionThe organic solution is then treated with charcoal
  14. customthe solvent is evaporated
  15. customto leave a residue which
  16. customis purified by chromatography

Sources & evidence

ORD record
ord-bcd2a7440a4649a5bebaadc8aec1b840
Source dataset
uspto-grants-1979_02
Patent number
US04138566

Reaction notes

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