Dimethylformamide → HCID 15230337, compound

HRID 1742592Notes

Reaction equation

HRID 1742592 reaction equation
[Cl:1][C:2]1[C:11]2[N:10]=[CH:9][CH:8]=[CH:7][C:6]=2[C:5]([S:12]([OH:15])(=[O:14])=O)=[CH:4][CH:3]=1.S(Cl)(Cl)=O.C[N:21]([CH3:24])[CH:22]=O>>[Cl:1][C:2]1[C:11]2[N:10]=[CH:9][CH:8]=[CH:7][C:6]=2[C:5]([S:12]([N:10]2[CH2:9][CH2:8][CH2:24][NH:21][CH2:22][CH2:11]2)(=[O:14])=[O:15])=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 190071168-Chloroquinoline-5-sulfonic acid

Product 1

HCID 15230337HCID 15230337, compoundYield 54%

Procedure

To 14.2 g of 8-chloro-5-quinolinesulfonic acid were added 142 ml of thionyl chloride and 1.42 ml of dimethylformamide, followed by heating under reflux for 3 hours. Then, the thionyl chloride was removed under reduced pressure and the resultant residue was dissolved in 100 ml of ice water. The pH of the resultant solution was adjusted at 6 with a saturated aqueous sodium hydrogencarbonate solution. The solution was subjected to extraction with 100 ml of dichloromethane. The resultant dichloromethane layer was added dropwise to 100 ml of a dichloromethane solution containing 5.81 g of homopiperazine and 5.6 g of triethylamine over a period of 30 minutes while cooling with ice. The mixture was stirred at a temperature of 15° C. to 20° C. for 2 hours, washed with a 200 ml of water, and dried over anhydrous magnesium sulfate. Then, the solvent was removed under reduced pressure to obtain a residue. The thus obtained residue was subjected to purification by means of a chromatography column packed with 500 g of silica gel (Wacogel C-200, manufactured by Wako Pure Chemicals Industries, Ltd., Japan) and using, as a solvent, a mixture of methanol and chloroform (5% methanol), to thereby obtain 10.2 g of 1-(8-chloro-5-quinolinesulfonyl)homopiperazine (54) (yield: 54%).

Workup

  1. temperatureby heating
  2. temperatureunder reflux for 3 hours
  3. customThen, the thionyl chloride was removed under reduced pressure
  4. dissolutionthe resultant residue was dissolved in 100 ml of ice water
  5. extractionThe solution was subjected to extraction with 100 ml of dichloromethane
  6. additionThe resultant dichloromethane layer was added dropwise to 100 ml of a dichloromethane solution
  7. additioncontaining 5.81 g of homopiperazine and 5.6 g of triethylamine over a period of 30 minutes
  8. temperaturewhile cooling with ice
  9. washwashed with a 200 ml of water
  10. dry with materialdried over anhydrous magnesium sulfate
  11. customThen, the solvent was removed under reduced pressure
  12. customto obtain a residue
  13. customThe thus obtained residue was subjected to purification by means of a chromatography column
  14. additiona mixture of methanol and chloroform (5% methanol)

Sources & evidence

ORD record
ord-0ebc37f1704b4dbbb438343d75c5b1a7
Source dataset
uspto-grants-1994_08
Patent number
US05340811

Reaction notes

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