Sodium Iodide → HCID 68527477, compound

HRID 1932528Notes

Reaction equation

HRID 1932528 reaction equation
[F:1][C:2]([F:26])([F:25])[C:3]1[CH:24]=[CH:23][C:6]([O:7][CH2:8][C:9]2[CH:10]=[CH:11][C:12]([O:15][C:16]3[CH:21]=[CH:20][C:19]([NH2:22])=[CH:18][CH:17]=3)=[N:13][CH:14]=2)=[CH:5][CH:4]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[Na+].Cl[CH2:36][C:37]([N:39]1[CH2:44][CH2:43][N:42]([CH2:45][C:46]2[CH:54]=[CH:53][C:52]3[O:51][CH2:50][O:49][C:48]=3[CH:47]=2)[CH2:41][CH2:40]1)=[O:38]>CN(C=O)C>[CH2:45]([N:42]1[CH2:41][CH2:40][N:39]([C:37](=[O:38])[CH2:36][NH:22][C:19]2[CH:20]=[CH:21][C:16]([O:15][C:12]3[CH:11]=[CH:10][C:9]([CH2:8][O:7][C:6]4[CH:23]=[CH:24][C:3]([C:2]([F:25])([F:1])[F:26])=[CH:4][CH:5]=4)=[CH:14][N:13]=3)=[CH:17][CH:18]=2)[CH2:44][CH2:43]1)[C:46]1[CH:54]=[CH:53][C:52]2[O:51][CH2:50][O:49][C:48]=2[CH:47]=1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 1537080HCID 1537080, compoundHCID 68525738HCID 68525738, compound

Product 1

HCID 68527477HCID 68527477, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

4-[5-(4-trifluoromethylphenoxymethyl)pyridin-2-yloxy]phenylamine (4.50 g, 12.5 mmol) was dissolved in DMF (150 mL). To the resulting solution were added potassium carbonate (2.60 g, 18.8 mmol) and sodium iodide (1.87 g, 12.5 mmol), and then to this solution was added 2-chloro-1-(4-piperonylpiperazin-1-yl)ethanone (4.21 g, 12.5 mmol). The resulting solution was stirred for 11 hours under a nitrogen atmosphere at 80° C. The resulting reaction solution was concentrated under reduced pressure. To the residue was added ethyl acetate and washed with a saturated sodium bicarbonate solution and brine. The organic layer was dried over anhydrous magnesium sulfate, and evaporated. The residue was purified by silica gel column chromatography (dichloromethane:methanol=80:1), to thereby yield 5.2 g of the title compound.

Workup

  1. customThe resulting reaction solution
  2. concentrationwas concentrated under reduced pressure
  3. additionTo the residue was added ethyl acetate
  4. washwashed with a saturated sodium bicarbonate solution and brine
  5. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  6. customevaporated
  7. customThe residue was purified by silica gel column chromatography (dichloromethane:methanol=80:1)

Sources & evidence

ORD record
ord-4d9f536d68834abd94e69eacfdfc32ac
Source dataset
uspto-grants-2012_05
Patent number
US08188277B2

Reaction notes

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