Piperazine → HCID 10982183, compound

HRID 1603587Notes

Reaction equation

HRID 1603587 reaction equation
Br[C:2]1[CH:7]=[C:6]([S:8]([C:11]2[CH:16]=[CH:15][C:14]([NH2:17])=[CH:13][CH:12]=2)(=[O:10])=[O:9])[CH:5]=[C:4]([Br:18])[N:3]=1.[NH:19]1[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]1.C(N(CC)CC)C>O1CCOCC1>[Br:18][C:4]1[CH:5]=[C:6]([S:8]([C:11]2[CH:16]=[CH:15][C:14]([NH2:17])=[CH:13][CH:12]=2)(=[O:10])=[O:9])[CH:7]=[C:2]([N:19]2[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]2)[N:3]=1

Participants

5

Reactant 3

HCID 4837PiperazineHCID 8471TriethylamineHCID 110146744-(2,6-dibromopyridin-4-yl)sulfonylaniline

Product 1

HCID 10982183HCID 10982183, compoundYield 82.7%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
40 °C

Procedure

0.275 g (0.0007 mol) of 4-(2,6-dibromopyridine-4-sulphonyl)-phenylamine was dissolved in 10 ml of dioxane and treated with 0.066 g (0.00077 mol) of piperazine and 1 ml of triethylamine. The mixture was stirred at 40° C. for 72 hrs. and the solvent was then removed. The residue was partitioned in ethyl acetate and water and the organic phase was extracted with sat. sodium chloride solution and dried over MgSO4 and filtered. After removal of the solvent the residue was chromatographed on silica gel with dichloromethane/methanol 9:1 and there was obtained 0.23 g (82%) of 4-(2-bromo-6-piperazin-1-ylpyridin-4-sulphonyl) -phenylamine as yellowish crystals; m.p.: 173-175° C.

Workup

  1. customand the solvent was then removed
  2. customThe residue was partitioned in ethyl acetate
  3. extractionwater and the organic phase was extracted with sat. sodium chloride solution
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customAfter removal of the solvent the residue
  7. customwas chromatographed on silica gel with dichloromethane/methanol 9:1

Sources & evidence

ORD record
ord-1f8bb73f991f4c5bb070ff7f5bddebe2
Source dataset
uspto-grants-1999_11
Patent number
US05990105

Reaction notes

Loading…