Morpholine → HCID 44464432, compound

HRID 453262Notes

Reaction equation

HRID 453262 reaction equation
Cl[CH2:2][CH2:3][O:4][C:5]1[CH:9]=[C:8]([CH3:10])[N:7]([C:11]2[CH:20]=[CH:19][C:18]3[C:13](=[CH:14][CH:15]=[C:16]([O:21][CH3:22])[CH:17]=3)[CH:12]=2)[N:6]=1.[NH:23]1[CH2:28][CH2:27][O:26][CH2:25][CH2:24]1>CN(C)C=O>[CH3:22][O:21][C:16]1[CH:17]=[C:18]2[C:13](=[CH:14][CH:15]=1)[CH:12]=[C:11]([N:7]1[C:8]([CH3:10])=[CH:9][C:5]([O:4][CH2:3][CH2:2][N:23]3[CH2:28][CH2:27][O:26][CH2:25][CH2:24]3)=[N:6]1)[CH:20]=[CH:19]2

Participants

4

Reactant 2

HCID 8083MorpholineHCID 46221334HCID 46221334, compound

Product 1

HCID 44464432HCID 44464432, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 3-(2-chloroethoxy)-5-methyl-1-(6-methoxynaphthalen-2-yl)-1H-pyrazol (0.63 g, 2 mmol) and morpholine (0.96 g, 8 mmol) in dimethylformamide (10 ml) was heated to 95° C., in a nitrogen atmosphere, during 20 hrs. Next, it was cooled, the DMF was evaporated in a rotavapor and water and dichloromethane was added to the residue. The organic phase was washed with water and, subsequently, it was extracted with HCl 2N several times. The collection of acidic waters was basified by the addition of NaOH 20% and it was extracted with dichloromethane, which was dried over Na2SO4, filtered and evaporated, thereby leaving a residue of 448 mg of 4-{2-[1-(6-methoxynaphthalen-2-yl)-5-methyl-1H-pyrazol-3-yloxy]ethyl}morpholine (yield: 61%) in the form of a colourless oil.

Workup

  1. temperatureNext, it was cooled
  2. customthe DMF was evaporated in a rotavapor and water and dichloromethane
  3. additionwas added to the residue
  4. washThe organic phase was washed with water
  5. extractionsubsequently, it was extracted with HCl 2N several times
  6. customThe collection of acidic waters
  7. additionwas basified by the addition of NaOH 20% and it
  8. extractionwas extracted with dichloromethane, which
  9. dry with materialwas dried over Na2SO4
  10. filtrationfiltered
  11. customevaporated

Sources & evidence

ORD record
ord-5ffa2aee62e5407d846a363629edd4ee
Source dataset
uspto-grants-2013_07
Patent number
US08492425B2

Reaction notes

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