Sodium Iodide → HCID 44464173, compound

HRID 453267Notes

Reaction equation

HRID 453267 reaction equation
[OH:1][C:2]1[CH:6]=[C:5]([CH3:7])[N:4]([C:8]2[CH:17]=[CH:16][C:15]3[C:10](=[CH:11][CH:12]=[CH:13][C:14]=3[O:18][CH3:19])[CH:9]=2)[N:3]=1.C([O-])([O-])=O.[K+].[K+].[Na+].[I-].Cl[CH2:29][CH2:30][N:31]1[CH2:36][CH2:35][O:34][CH2:33][CH2:32]1>CN(C)C=O>[CH3:19][O:18][C:14]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:15]=1[CH:16]=[CH:17][C:8]([N:4]1[C:5]([CH3:7])=[CH:6][C:2]([O:1][CH2:29][CH2:30][N:31]3[CH2:36][CH2:35][O:34][CH2:33][CH2:32]3)=[N:3]1)=[CH:9]2

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 767274-(2-Chloroethyl)morpholineHCID 178488641HCID 178488641, compound

Product 1

HCID 44464173HCID 44464173, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 3-hydroxy-5-methyl-1-(5-methoxynaphthalen-2-yl)-1H-pyrazol (150 mg, 0.59 mmol) in dimethylformamide (10 ml), 2-chloroethylmorpholine chlorhydrate (136 mg, 0.71 mmol), K2CO3 (245 mg, 1.77 mmol), and NaI (catalytic quantity) were added. The mixture was heated, in an inert nitrogen atmosphere, at 90° C. during 8 hrs. Subsequently it was cooled, filtered, and the filtered product was evaporated to dryness in a rotavapor. The residue was divided between water and ethylic ether. The organic phase was washed with water and afterwards with an aqueous solution of HCl 2N several times. The collection of the acidic aqueous phases were basified with a solution of NaOH 20% and it was extracted with ethyl acetate, which was washed with water, dried over sodium sulfate, filtered, and evaporated to dryness yielding 204 mg (94%) of 4-{2-[1-(5-methoxynaphthalen-2-yl)-5-methyl-1H-pyrazol-3-yloxy]ethyl}morpholine in the form of an oil.

Workup

  1. temperatureSubsequently it was cooled
  2. filtrationfiltered
  3. customthe filtered product was evaporated to dryness in a rotavapor
  4. washThe organic phase was washed with water and afterwards with an aqueous solution of HCl 2N several times
  5. customThe collection of the acidic aqueous phases
  6. extractionwas extracted with ethyl acetate, which
  7. washwas washed with water
  8. dry with materialdried over sodium sulfate
  9. filtrationfiltered
  10. customevaporated to dryness

Sources & evidence

ORD record
ord-44ac6d514ba14ab1ba63d4d07f6a9261
Source dataset
uspto-grants-2013_07
Patent number
US08492425B2

Reaction notes

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