p-Toluenesulfonic acid → HCID 70608556, compound

HRID 1863464Notes

Reaction equation

HRID 1863464 reaction equation
[N:1]1([CH2:8][CH2:9][CH2:10][OH:11])[CH2:7][CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[CH3:12][O:13][C:14]1[C:24]([O:25][CH3:26])=[C:23]([O:27][CH3:28])[CH:22]=[CH:21][C:15]=1[CH:16]=[CH:17][C:18]([OH:20])=[O:19].C1(C)C=CC(S(O)(=O)=O)=CC=1.[C:40]([O-:45])(=[O:44])[C:41]([O-:43])=[O:42]>C1C=CC=CC=1>[C:40]([OH:45])(=[O:44])[C:41]([OH:43])=[O:42].[CH3:12][O:13][C:14]1[C:24]([O:25][CH3:26])=[C:23]([O:27][CH3:28])[CH:22]=[CH:21][C:15]=1[CH:16]=[CH:17][C:18]([OH:20])=[O:19].[N:1]1([CH2:8][CH2:9][CH2:10][OH:11])[CH2:7][CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 71081OxalateHCID 1184003-(2,3,4-Trimethoxyphenyl)-2-propenoic acidHCID 135569423-(1,4-Diazepan-1-yl)propan-1-ol

Product 1

HCID 70608556HCID 70608556, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

In 1.50 ml of absolute benzene there were dissolved 1.58 g of 1-homopiperazinepropanol, 3.09 g of 2,3,4-trimethoxycinnamic acid and 9.5 g of p-toluene sulfonic acid. The solution 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% hydrochloric acid. After the aqueous layer was washed with ether, the system was rendered alkaline with potassium carbonate followed by extraction with ether. After the ethereal layer was dehydrated over 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 oxalate thereof in accordance with conventional manner. Upon recrystallization from methanol, 1-homopiperazinepropanol 2,3,4-trimethoxycinnamate oxalate was obtained having a melting point of 156°-158° C. The yield was 48%.

Workup

  1. temperatureThe solution 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% hydrochloric acid
  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 methanol

Sources & evidence

ORD record
ord-40948de47aa14628b1f969324dd8b36a
Source dataset
uspto-grants-1979_09
Patent number
US04169144

Reaction notes

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