Sodium Iodide → HCID 68524311, compound

HRID 884167Notes

Reaction equation

HRID 884167 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([O:8][C:9]2[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][C:17]([N:19]3[CH2:24][CH2:23][N:22]([CH2:25][C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)[CH2:21][CH2:20]3)=[O:18])=[CH:11][CH:10]=2)=[N:6][CH:7]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[Na+].[CH2:40](Br)[C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1>CN(C=O)C>[CH2:25]([N:22]1[CH2:21][CH2:20][N:19]([C:17](=[O:18])[CH2:16][CH2:15][C:12]2[CH:13]=[CH:14][C:9]([O:8][C:5]3[CH:4]=[CH:3][C:2]([N:1]([CH2:15][C:12]4[CH:13]=[CH:14][CH:9]=[CH:10][CH:11]=4)[CH2:40][C:41]4[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=4)=[CH:7][N:6]=3)=[CH:10][CH:11]=2)[CH2:24][CH2:23]1)[C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 68525829HCID 68525829, compound

Product 1

HCID 68524311HCID 68524311, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-[4-(5-aminopyridin-2-yloxy)phenyl]-1-(4-benzylpiperazin-1-yl)propane-1-one (1.0 g, 2.4 mmol) was dissolved in DMF (30 mL). To this solution were added potassium carbonate (0.73 g, 5.28 mmol), sodium iodide (0.76 g, 5.04 mmol) and benzyl bromide (0.60 mL, 5.04 mmol), and the resulting solution was stirred at room temperature overnight. This reaction solution was concentrated under reduced pressure. The residue was diluted with chloroform, and washed with water, saturated sodium bicarbonate solution and brine. The organic layer was dried over anhydrous magnesium sulfate, and evaporated. The residue was then purified by silica gel column chromatography (chloroform methanol=80:1), to thereby yield 0.67 g of the title compound.

Workup

  1. concentrationThis reaction solution was concentrated under reduced pressure
  2. additionThe residue was diluted with chloroform
  3. washwashed with water, saturated sodium bicarbonate solution and brine
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. customevaporated
  6. customThe residue was then purified by silica gel column chromatography (chloroform methanol=80:1)

Sources & evidence

ORD record
ord-8e8e461615934f0fb185db16766d911f
Source dataset
uspto-grants-2012_08
Patent number
US08236826B2

Reaction notes

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