p-Toluenesulfonic acid → HCID 70607338, compound

HRID 1576298Notes

Reaction equation

HRID 1576298 reaction equation
[N:1]1([CH2:7][CH2:8][OH:9])[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[CH3:10][O:11][C:12]1[C:20]([O:21][CH3:22])=[C:19]([O:23][CH3:24])[CH:18]=[CH:17][C:13]=1[C:14]([OH:16])=[O:15].C1(C)C=CC(S(O)(=O)=O)=CC=1.[C:36]([OH:43])(=[O:42])/[CH:37]=[CH:38]\[C:39]([OH:41])=[O:40]>C1C=CC=CC=1>[C:36]([OH:43])(=[O:42])/[CH:37]=[CH:38]\[C:39]([OH:41])=[O:40].[CH3:10][O:11][C:12]1[C:20]([O:21][CH3:22])=[C:19]([O:23][CH3:24])[CH:18]=[CH:17][C:13]=1[C:14]([OH:16])=[O:15].[N:1]1([CH2:7][CH2:8][OH:9])[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 76771-(2-Hydroxyethyl)piperazineHCID 113082,3,4-Trimethoxybenzoic acidHCID 444266Maleic Acid

Product 1

HCID 70607338HCID 70607338, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

In 150 ml of absolute benzene there were dissolved 2.6 g of 1-piperazineethanol, 5.5 g of 2,3,4-trimethoxybenzoic acid and 19 g of p-toluene sulfonic acid. The solution was heated for 15 hours to reflux while removing the formed water. After the reaction liquid was cooled, the reaction liquid was washed with 15% potassium carbonate and then extracted with 10% hydrochloric acid. After washing the aqueous layer with ether, the system was rendered alkaline with potassium carbonate followed by extraction with ether. The ethereal layer was dehydrated with a Glauber's salt and then the ether was removed by distillation. The resultant residue was subjected to chromatography using silica gel to give a colorless transparent liquid. The liquid was treated in a conventional manner to convert the product into the maleic acid salt thereof. Upon crystallization from ethanol, 1-piperazineethanol 2,3,4-trimethoxybenzoate maleate was obtained exhibiting a melting point of 140°-141°C. The Yield was 46%.

Workup

  1. temperatureThe solution was heated for 15 hours
  2. temperatureto reflux
  3. customwhile removing the formed water
  4. customAfter the reaction liquid
  5. temperaturewas cooled
  6. customthe reaction liquid
  7. washwas washed with 15% potassium carbonate
  8. extractionextracted with 10% hydrochloric acid
  9. washAfter washing the aqueous layer with ether
  10. extractionfollowed by extraction with ether
  11. customthe ether was removed by distillation
  12. customto give a colorless transparent liquid
  13. additionThe liquid was treated in a conventional manner
  14. customUpon crystallization from ethanol

Sources & evidence

ORD record
ord-b2a0f0c55d7a4ebebd205d87b46c3195
Source dataset
uspto-grants-1976_09
Patent number
US03980643

Reaction notes

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