Hydrochloric Acid → HCID 70608254, compound

HRID 1863463Notes

Reaction equation

HRID 1863463 reaction equation
[N:1]1([CH2:7][CH2:8][OH:9])[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.C1(C)C=CC(S(O)(=O)=O)=CC=1.[C:21](O)(=[O:30])[CH:22]=[CH:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.[ClH:32]>C1C=CC=CC=1>[ClH:32].[C:21]([O:9][CH2:8][CH2:7][N:1]1[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1)(=[O:30])[CH:22]=[CH:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6101p-Toluenesulfonic acidHCID 76771-(2-Hydroxyethyl)piperazineHCID 87842-Propenoic acid, 3-phenyl-

Product 1

HCID 70608254HCID 70608254, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

In 150 ml of absolute benzene there were dissolved 1.95 g of 1-piperazineethanol and 14.2 g of p-toluene sulfonic acid. To the solution 2.89 g of cinnamic 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% hydrochloric acid. After the aqueous layer was washed with ether, the system was rendered alkaline 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 give a colorless transparent liquid. The liquid was converted into the hydrochloride thereof. Upon recrystallization from ethanol, 1-piperazineethanol cinnamate hydrochloride was obtained. The melting point of the product was 184°-187° C. The yield was 53%.

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% 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 give a colorless transparent liquid
  12. customUpon recrystallization from ethanol

Sources & evidence

ORD record
ord-f3561142b7f54b60aae93a83b221c2dc
Source dataset
uspto-grants-1979_09
Patent number
US04169144

Reaction notes

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