Potassium Iodide → HCID 19837167, compound

HRID 2050682Notes

Reaction equation

HRID 2050682 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:23]=[C:24]([O:28][CH3:29])[C:25]=1[O:26][CH3:27])[C:6]1[O:7][C:8]2[C:13]([C:14](=[O:22])[C:15]=1[C:16]([NH:18][CH2:19][CH2:20]Br)=[O:17])=[CH:12][CH:11]=[CH:10][CH:9]=2.[I-].[K+].[N:32]1[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=1[N:38]1[CH2:43][CH2:42][NH:41][CH2:40][CH2:39]1.C(=O)([O-])[O-].[Na+].[Na+]>ClCCl.O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:23]=[C:24]([O:28][CH3:29])[C:25]=1[O:26][CH3:27])[C:6]1[O:7][C:8]2[C:13]([C:14](=[O:22])[C:15]=1[C:16]([NH:18][CH2:19][CH2:20][N:41]1[CH2:42][CH2:43][N:38]([C:33]3[CH:34]=[CH:35][CH:36]=[CH:37][N:32]=3)[CH2:39][CH2:40]1)=[O:17])=[CH:12][CH:11]=[CH:10][CH:9]=2

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 10340Sodium CarbonateHCID 944591-(2-Pyridyl)piperazineHCID 54368735HCID 54368735, compound

Product 1

HCID 19837167HCID 19837167, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

0.2 g of 3',4',5'-trimethoxy-3-(2-bromoethylamino-carbonyl) flavone were dissolved in 10 ml dichloromethane, and the solution was reacted with a spatula tip full of potassium iodide and 0.5 ml 1-(2-pyridyl)-piperazine. The reaction mixture was heated at reflux temperature for one hour. After cooling, the reaction mixture was worked up by adding further dichloromethane and shaking with saturated sodium carbonate solution and water. Then the organic phase was dried over sodium sulfate, concentrated, and the residue was purified by column chromatography on silica gel under slightly elevated pressure (flash chromatography) using tetrahydrofuran/ethylacetate 1:1 as the eluent. In this way 3',4',5'-trimethoxy-3-{2-[4-(2-pyridyl)-piperazin-1-yl]-ethylamino-carbonyl) flavone was obtained in pure amorphous form.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux temperature for one hour
  3. temperatureAfter cooling
  4. dry with materialThen the organic phase was dried over sodium sulfate
  5. concentrationconcentrated
  6. customthe residue was purified by column chromatography on silica gel under slightly elevated pressure (flash chromatography)

Sources & evidence

ORD record
ord-cf6d6098519949f2873081360d2e1c93
Source dataset
uspto-grants-1991_05
Patent number
US05013852

Reaction notes

Loading…