Sodium Iodide → HCID 16730082, compound

HRID 1095428Notes

Reaction equation

HRID 1095428 reaction equation
Br[CH2:2][CH2:3][O:4][CH2:5][CH2:6][O:7][C:8]1[CH:12]=[CH:11][N:10]([C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[C:15]([Cl:20])[CH:14]=2)[N:9]=1.[NH:21]1[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1.C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>CN(C)C=O>[Cl:20][C:15]1[CH:14]=[C:13]([N:10]2[CH:11]=[CH:12][C:8]([O:7][CH2:6][CH2:5][O:4][CH2:3][CH2:2][N:21]3[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]3)=[N:9]2)[CH:18]=[CH:17][C:16]=1[Cl:19]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 8082PiperidineHCID 11430Potassium CarbonateHCID 57861963HCID 57861963, compound

Product 1

HCID 16730082HCID 16730082, compoundYield 68.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 3-(2-(2-bromoethoxy)ethoxy)-1-(3,4-dichlorophenyl)-1H-pyrazole (0.17 mg, 0.45 mmol), piperidine (62 mg, 0.72 mmol), potassium carbonate (0.25 g, 1.8 mmol) and sodium iodide (67 mg, 0.45 mmol) in dimethylformamide (5 ml) was stirred at 100° C. overnight in a dry nitrogen atmosphere. The solvent was evaporated in vacuo and water and ethyl ether was added. The aqueous phase was extracted several times with organic solvent and the combined organic phases washed with water, dried over sodium sulphate, filtered and evaporated to dryness in vacuo. The crude dark oil obtained, 138 mg, was purified by column chromatography on silica gel (eluent: ethyl acetate/petroleum ether 2:8 to 10:0 and ethyl acetate/CH3OH 9:1) yielding 118 mg of 1-(2-(2-(1-(3,4-dichlorophenyl)-1H-pyrazol-3-yloxy)ethoxy)ethyl)piperidine as an oil

Workup

  1. customThe solvent was evaporated in vacuo and water and ethyl ether
  2. additionwas added
  3. extractionThe aqueous phase was extracted several times with organic solvent
  4. washthe combined organic phases washed with water
  5. dry with materialdried over sodium sulphate
  6. filtrationfiltered
  7. customevaporated to dryness in vacuo
  8. customThe crude dark oil obtained
  9. custom138 mg, was purified by column chromatography on silica gel (eluent: ethyl acetate/petroleum ether 2:8 to 10:0 and ethyl acetate/CH3OH 9:1)

Sources & evidence

ORD record
ord-12df31cc2b974f11a7860beedd0d2722
Source dataset
uspto-grants-2012_03
Patent number
US08138186B2

Reaction notes

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