1-(2-Hydroxyethyl)piperazine → HCID 70115076, compound

HRID 1376796Notes

Reaction equation

HRID 1376796 reaction equation
[Cl:1][CH2:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:12])[C:6]2=[CH:13][C:14]1[C:22]2[C:17](=[N:18][CH:19]=[CH:20][CH:21]=2)[NH:16][CH:15]=1.[OH:23][CH2:24][CH2:25][N:26]1[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]1.[OH-].[Na+]>>[ClH:1].[OH:23][CH2:24][CH2:25][N:26]1[CH2:31][CH2:30][N:29]([CH2:2][C:3]2[CH:4]=[C:5]3[C:9](=[CH:10][CH:11]=2)[NH:8][C:7](=[O:12])[C:6]3=[CH:13][C:14]2[C:22]3[C:17](=[N:18][CH:19]=[CH:20][CH:21]=3)[NH:16][CH:15]=2)[CH2:28][CH2:27]1

Participants

4

Reactant 3

HCID 76771-(2-Hydroxyethyl)piperazineHCID 14798Sodium HydroxideHCID 86751208HCID 86751208, compound

Product 1

HCID 70115076HCID 70115076, compound

Procedure

A mixture of 5-(chloromethyl)-3-[(7-azaindol-3-yl) methylene]-2-oxindole (3.098 g, 10 mmol), 4-hydroxyethyl-piperazine (2.604 g, 20 mmol) in 1N NaOH (20 ml, 20 mmol) was refluxed for 48 h. The cooled reaction mixture was extracted with ether, and the ether extract was shaken with diluted hydrochloric acid. The aqueous acid layer was made alkaline with potassium carbonate and extracted with ether. Addition of hydrogen chloride to the dried ether extract precipitated a crude hydrochloride which was crystallized twice from a mixture of methanol and ether.

Workup

  1. temperaturewas refluxed for 48 h
  2. customThe cooled reaction mixture
  3. extractionwas extracted with ether
  4. extractionthe ether extract
  5. extractionextracted with ether
  6. additionAddition of hydrogen chloride to the dried ether
  7. extractionextract
  8. customprecipitated a crude hydrochloride which
  9. customwas crystallized twice from a mixture of methanol and ether

Sources & evidence

ORD record
ord-e5a4d0da5167418daa4c4161c7def2e4
Source dataset
uspto-grants-1997_09
Patent number
US05663346

Reaction notes

Loading…