Sodium Iodide → HCID 11373812, compound

HRID 2211824Notes

Reaction equation

HRID 2211824 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:12][CH2:11][CH:10]([O:13][C:14]3[C:15](Br)=[N:16][CH:17]=[CH:18][CH:19]=3)[C:9]2=[O:21])=[CH:4][CH:3]=1.[CH3:22][N:23]1[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]1.[I-].[Na+].O1CCOCC1>C(OCC)(=O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:12][CH2:11][CH:10]([O:13][C:14]3[C:15]([N:26]4[CH2:27][CH2:28][N:23]([CH3:22])[CH2:24][CH2:25]4)=[N:16][CH:17]=[CH:18][CH:19]=3)[C:9]2=[O:21])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 312751,4-DioxaneHCID 531671-MethylpiperazineHCID 21963146HCID 21963146, compound

Product 1

HCID 11373812HCID 11373812, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a 100 mL round-bottomed flask equipped with condenser and N2 inlet were added 1.15 g (2.79 mmol) of 1-(4-bromo-phenyl)-3-(2-bromo-pyridin-3-yloxy)-pyrrolidin-2-one, 1.6 mL (13.96 mmol) 1-methylpiperazine, 0.418 g (2.79 mmol) sodium iodide, and 20 mL dioxane. The reaction was refluxed 5 days, cooled, taken up in ethyl acetate, washed with water, dried over sodium sulfate, and evaporated. The residue was chromatographed on silica gel using methanol/ethyl acetate to afford the desired product in 35% yield as a foam, which was converted to the hydrochloride salt, mp 72–82° C.

Workup

  1. customTo a 100 mL round-bottomed flask equipped with condenser and N2 inlet
  2. temperatureThe reaction was refluxed 5 days
  3. temperaturecooled
  4. washwashed with water
  5. dry with materialdried over sodium sulfate
  6. customevaporated
  7. customThe residue was chromatographed on silica gel

Sources & evidence

ORD record
ord-2173a87fa5a0460580c2f8d76f857c79
Source dataset
uspto-grants-2006_09
Patent number
US07101885B2

Reaction notes

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