p-Toluenesulfonic acid → HCID 86733975, compound

HRID 1863460Notes

Reaction equation

HRID 1863460 reaction equation
C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH3:12][O:13][C:14]1[C:22]([O:23][CH3:24])=[C:21]([O:25][CH3:26])[CH:20]=[CH:19][C:15]=1[C:16]([OH:18])=[O:17].[C:27]([OH:34])(=[O:33])/[CH:28]=[CH:29]\[C:30]([OH:32])=[O:31].[N:35]1([CH2:42][CH2:43][OH:44])[CH2:41][CH2:40][CH2:39][NH:38][CH2:37][CH2:36]1>C1C=CC=CC=1>[C:27]([OH:34])(=[O:33])/[CH:28]=[CH:29]\[C:30]([OH:32])=[O:31].[CH3:12][O:13][C:14]1[C:22]([O:23][CH3:24])=[C:21]([O:25][CH3:26])[CH:20]=[CH:19][C:15]=1[C:16]([OH:18])=[O:17].[N:35]1([CH2:42][CH2:43][OH:44])[CH2:41][CH2:40][CH2:39][NH:38][CH2:37][CH2:36]1

Participants

6

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 113082,3,4-Trimethoxybenzoic acidHCID 444266Maleic AcidHCID 27365502-(1,4-Diazepan-1-yl)ethan-1-ol

Product 1

HCID 86733975HCID 86733975, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

In 150 ml of absolute benzene there were dissolved 1.44 of 1-homopiperazineethanol and 9.5 g of p-toluene sulfonic acid. To the resulting solution, 2.75 g of 2,3,4-trimethoxybenzoic acid was added. The system was heated for 16 hours to reflux while removing the formed water. The reaction liquid was cooled, washed with 15% potassium carbonate and then extracted with 10% HCl. After the aqueous layer was washed and then rendered alkaline with potassium carbonate, followed by extraction with ether. After the ethereal layer was dehydrated with a Glauber's salt, the ether was distilled off. The resultant residue was subjected to chromatography using silica gel to obtain a colorless transparent liquid. The liquid was converted into the maleic acid salt thereof in accordance with a conventional manner. Upon recrystallization from ethanol, 1-homopiperazineethanol 2,3,4-trimethoxybenzoate maleate was obtained having a melting point of 112°-113° C. The yield was 59%.

Workup

  1. temperatureThe system was heated for 16 hours
  2. temperatureto reflux
  3. customwhile removing the formed water
  4. customThe reaction liquid
  5. temperaturewas cooled
  6. washwashed with 15% potassium carbonate
  7. extractionextracted with 10% HCl
  8. washAfter the aqueous layer was washed
  9. extractionfollowed by extraction with ether
  10. distillationthe ether was distilled off
  11. customto obtain a colorless transparent liquid
  12. customUpon recrystallization from ethanol

Sources & evidence

ORD record
ord-4f518f6f67264fec8b5806ff1c448eaf
Source dataset
uspto-grants-1979_09
Patent number
US04169144

Reaction notes

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