p-Toluenesulfonic acid → HCID 86733975, compound

HRID 1834058Notes

Reaction equation

HRID 1834058 reaction equation
[N:1]1([CH2:8][CH2:9][OH:10])[CH2:7][CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH3:22][O:23][C:24]1[C:32]([O:33][CH3:34])=[C:31]([O:35][CH3:36])[CH:30]=[CH:29][C:25]=1[C:26]([OH:28])=[O:27].[C:37]([OH:44])(=[O:43])/[CH:38]=[CH:39]\[C:40]([OH:42])=[O:41]>C1C=CC=CC=1>[C:37]([OH:44])(=[O:43])/[CH:38]=[CH:39]\[C:40]([OH:42])=[O:41].[CH3:22][O:23][C:24]1[C:32]([O:33][CH3:34])=[C:31]([O:35][CH3:36])[CH:30]=[CH:29][C:25]=1[C:26]([OH:28])=[O:27].[N:1]1([CH2:8][CH2:9][OH:10])[CH2:7][CH2:6][CH2:5][NH:4][CH2:3][CH2:2]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 1.44g 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 with ether 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 with ether
  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-7f636e5931b6485db9970cc3630679ec
Source dataset
uspto-grants-1978_01
Patent number
US04068069

Reaction notes

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