Dimethyl Sulfoxide → HCID 14326854, compound

Temperature

-55 °C

To 100 ml of a dried dichloromethane solution containing 2.67 g of oxalyl chloride was added dropwise at -50° C. 20 ml of a dichloromethane solution containing 1.64 g of dimethylsulfoxide. The mixture was allowed to stand for 5 minutes. To the mixture was added dropwise over a period of 10 minutes, while maintaining the temperature at -55° C., 40 ml of a dried dichloromethane solution containing 5.84 g of 1-(5-isoquinolinesulfonyl)-4-hydroxypiperidine as obtained in Example 7, followed by stirring at that temperature for 20 minutes. To the resulting mixture was added 1.4 ml of triethylamine, and the mixture was stirred for 5 minutes. Then, the temperature of the mixture was raised to 15° C. The mixture was washed twice with 100 ml each of water and dried with anhydrous sodium sulfate. Then, the dichloromethane was removed under reduced pressure to obtain a residue. The residue thus obtained was subjected to purification by silica gel column chromatography (Wacogel C-200, 150 g; solvent: chloroform) to obtain 5.16 g of 1-(5-isoquinolinesulfonyl)-4-piperidone.

1. additionwas added dropwise at -50° C
2. additionTo the mixture was added dropwise over a period of 10 minutes
3. customas obtained in Example 7
4. stirringthe mixture was stirred for 5 minutes
5. temperatureThen, the temperature of the mixture was raised to 15° C
6. washThe mixture was washed twice with 100 ml each of water
7. dry with materialdried with anhydrous sodium sulfate
8. customThen, the dichloromethane was removed under reduced pressure
9. customto obtain a residue
10. customThe residue thus obtained
11. customwas subjected to purification by silica gel column chromatography (Wacogel C-200, 150 g; solvent: chloroform)

ORD record

ord-20543cc4eb884a5aa5e1b520c34a3340

Source dataset

uspto-grants-1989_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04798897