Hydrochloric Acid → HCID 70607102, compound

HRID 1834059Notes

Reaction equation

HRID 1834059 reaction equation
[N:1]1([CH2:7][CH2:8][CH2:9][OH:10])[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[C:11](O)(=[O:18])[C:12]1[CH:17]=[CH:16][N:15]=[CH:14][CH:13]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1.[ClH:31]>C1C=CC=CC=1>[ClH:31].[C:11]([O:10][CH2:9][CH2:8][CH2:7][N:1]1[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1)(=[O:18])[C:12]1[CH:17]=[CH:16][N:15]=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 5922Isonicotinic AcidHCID 6101p-Toluenesulfonic acidHCID 79207Piperazin-1-ylpropanol

Product 1

HCID 70607102HCID 70607102, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

In 150 ml of absolute benzene there were dissolved 2.88 g of 1-piperazinepropanol, 3.2 g of isonicotinic acid and 30.4 g of p-toluene sulfonic acid. The resulting solution was heated for 15 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 and then extracted 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. This liquid was converted to the hydrochloride thereof in accordance with a conventional manner. It was recrystallized from ethanol to give 1-piperazinepropanol isonicotinate hydrochloride. The melting point of the product was 201°-202° C. The Yield was 66%.

Workup

  1. temperatureThe resulting solution was heated for 15 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. extractionextracted with ether
  10. distillationthe ether was distilled off
  11. customto obtain a colorless transparent liquid
  12. customIt was recrystallized from ethanol

Sources & evidence

ORD record
ord-0e2ddfc7dbc149da9f7a5c17fb5ba3cf
Source dataset
uspto-grants-1978_01
Patent number
US04068069

Reaction notes

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