Picolinic acid → HCID 86733976, compound

HRID 1834060Notes

Reaction equation

HRID 1834060 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.[N:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[C:18]([OH:20])=[O:19].C1(C)C=CC(S(O)(=O)=O)=CC=1.[C:32]([OH:39])(=[O:38])/[CH:33]=[CH:34]\[C:35]([OH:37])=[O:36]>C1C=CC=CC=1>[C:32]([OH:39])(=[O:38])/[CH:33]=[CH:34]\[C:35]([OH:37])=[O:36].[N:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[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 1018Picolinic acidHCID 6101p-Toluenesulfonic acidHCID 444266Maleic AcidHCID 135569423-(1,4-Diazepan-1-yl)propan-1-ol

Product 1

HCID 86733976HCID 86733976, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

In 150 ml of absolute benzene there were dissolved 3.04 g of 1-homopiperazinepropanol, 2.85 g of picolinic acid and 2.73 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. The aqueous layer was washed with ether, then 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 give a colorless transparent liquid. The liquid was converted into the maleic acid salt thereof in accordance with a conventional manner. Upon recrystallization of the maleic acid salt from ethanol, 1-homopiperazinepropanol picolinate maleate was obtained having a melting point of 105°-107° C. The Yield was 47%.

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. washThe 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 of the maleic acid salt from ethanol

Sources & evidence

ORD record
ord-7d362302dd3e480d8d02996ab96ee1e8
Source dataset
uspto-grants-1978_01
Patent number
US04068069

Reaction notes

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