Sodium Iodide → HCID 15485488, compound

HRID 369434Notes

Reaction equation

HRID 369434 reaction equation
Cl[CH2:2][CH2:3][CH2:4][O:5][C:6]1[C:15](=[O:16])[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH:13]=2)[O:8][C:7]=1[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.[N:28]1[C:37]2[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=2)[CH:31]=[CH:30][C:29]=1[CH2:38][N:39]1[CH2:44][CH2:43][NH:42][CH2:41][CH2:40]1.C(=O)([O-])O.[Na+].[I-].[Na+]>CC(=O)CC>[CH2:20]([O:19][C:17]([C:12]1[CH:13]=[C:14]2[C:9](=[CH:10][CH:11]=1)[O:8][C:7]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[C:6]([O:5][CH2:4][CH2:3][CH2:2][N:42]1[CH2:43][CH2:44][N:39]([CH2:38][C:29]3[CH:30]=[CH:31][C:32]4[C:37](=[CH:36][CH:35]=[CH:34][CH:33]=4)[N:28]=3)[CH2:40][CH2:41]1)[C:15]2=[O:16])=[O:18])[CH3:21]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 516892Sodium BicarbonateHCID 43753132-(1-Piperazinylmethyl)quinolineHCID 23286062HCID 23286062, compound

Product 1

HCID 15485488HCID 15485488, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

3-(3-Chloropropoxy)-6-ethoxycarbonylflavone (1.2 mmol), 1-(2-quinolinylmethyl)piperazine (0.32 g, 1.2 mmol), sodium hydrogencarbonate (0.31 g, 2.9 mmol) and sodium iodide (0.43 g, 2.9 mmol) were dissolved in 25 ml of 2-butanone, followed by overnight refluxing. The reaction mixture was concentrated under reduced pressure. Chloroform was added to the residue, and an insoluble matter was removed. The filtrate was concentrated under reduced pressure. The residue was purified by chromatography on a silica gel column (ethyl acetate:methanol=5:1), whereby the title compound represented by the following formula was obtained as a brown oil (yield: 75%). ##STR64##

Workup

  1. temperaturerefluxing
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. additionChloroform was added to the residue
  4. customan insoluble matter was removed
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. customThe residue was purified by chromatography on a silica gel column (ethyl acetate:methanol=5:1), whereby the title compound

Sources & evidence

ORD record
ord-23b495d70d31451db579e31d34946c0d
Source dataset
uspto-grants-2000_10
Patent number
US06136848

Reaction notes

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