Chloroform → HCID 23368060, compound

291 mg (1.5 mmol) of 2-(2-hydroxyethoxy)-5,6,7,8-tetrahydroquinoxaline was dissolved in 15 ml of methylene chloride. To the resultant solution was added 0.25 ml (1.8 mmol) of triethylamine and then, 0.13 ml (1.65 mmol) of methanesulfonyl chloride was added dropwise thereto. The resultant mixture was stirred at room temperature for 2.5 hours to effect a reaction. To the resultant reaction mixture was added chloroform to obtain a mixture. The mixture was extracted with an aqueous potassium carbonate solution to thereby obtain an organic layer and an aqueous layer. The aqueous layer was subjected to extraction with chloroform to obtain an additional organic layer. The two organic layers were combined, dried over sodium sulfate, and subjected to filtration, followed by concentration, to thereby obtain 408 mg of 2-(2-methanesulfonyloxyethoxy) -5,6,7,8-tetrahydroquinoxaline. The thus obtained 2-(2-methanesulfonyloxyethoxy)-5,6,7,8-tetrahydroquinoxaline was dissolved in 10 ml of acetonitrile. To the resultant solution were added 0.31 g (2.25 mmol) of potassium carbonate and 294 mg (1.8 mmol) of 1-(2-pyridyl)piperazine, and the resultant mixture was heated under reflux for 24 hours. Then, the mixture was subjected to filtration to filter off insoluble substances, which were then washed with acetonitrile, to thereby obtain a filtrate. The solvent of the filtrate was distilled off in vacuo to thereby obtain a residue. The obtained residue was purified by silica gel column chromatography. That is, the residue was charged in a column of 20 g of silica gel (Art7734, manufactured and sold by E. Merck, Darmstadt) and eluted with chloroform-methanol (100:1), to thereby obtain 522 mg of 2-[2-{4-(2-pyridyl)-1-piperazinyl}ethoxy]-5,6,7,8-tetrahydroquinoxaline (compound 517) (yield: 100%).

1. customa reaction
2. customTo the resultant reaction mixture
3. customto obtain a mixture
4. extractionThe mixture was extracted with an aqueous potassium carbonate solution
5. customto thereby obtain an organic layer
6. extractionThe aqueous layer was subjected to extraction with chloroform
7. customto obtain an additional organic layer
8. dry with materialdried over sodium sulfate
9. filtrationsubjected to filtration
10. concentrationfollowed by concentration

ORD record

ord-c8e990dc6f79456d920d19039270b4bb

Source dataset

uspto-grants-1996_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05578596