Water → {3-(3-Methoxy-1,2,4-oxadiazol-5-yl)-5-[4-(trifluoromethyl)phenyl]piperidin-1-yl}(morpholin-4-yl)methanone

HRID 661284Notes

Reaction equation

HRID 661284 reaction equation
Cl[C:2]1[N:6]=[C:5]([CH:7]2[CH2:12][CH:11]([C:13]3[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][CH:14]=3)[CH2:10][N:9]([C:23]([N:25]3[CH2:30][CH2:29][O:28][CH2:27][CH2:26]3)=[O:24])[CH2:8]2)[O:4][N:3]=1.[CH3:31][O-:32].[Na+].O>CO>[CH3:31][O:32][C:2]1[N:6]=[C:5]([CH:7]2[CH2:12][CH:11]([C:13]3[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][CH:14]=3)[CH2:10][N:9]([C:23]([N:25]3[CH2:30][CH2:29][O:28][CH2:27][CH2:26]3)=[O:24])[CH2:8]2)[O:4][N:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 10942334Sodium MethoxideHCID 58116540{3-(3-Chloro-1,2,4-oxadiazol-5-yl)-5-[4-(trifluoromethyl)phenyl]piperidin-1-yl}(morpholin-4-yl)methanone

Product 1

HCID 58116563{3-(3-Methoxy-1,2,4-oxadiazol-5-yl)-5-[4-(trifluoromethyl)phenyl]piperidin-1-yl}(morpholin-4-yl)methanone

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 100 mg (0.225 mmol) of the oxadiazole from Example 23A in 8.0 ml of methanol were added 60.79 mg (1.124 mmol) of sodium methoxide, and then the reaction mixture was stirred under reflux for 18 h. The reaction mixture was admixed with water and extracted with dichloromethane. The organic phase was dried over magnesium sulphate, filtered and concentrated under reduced pressure. The crude product was purified by means of preparative HPLC. Yield: 32.0 mg (31% of theory)

Workup

  1. temperatureunder reflux for 18 h
  2. extractionextracted with dichloromethane
  3. dry with materialThe organic phase was dried over magnesium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe crude product was purified by means of preparative HPLC

Sources & evidence

ORD record
ord-9b712d9ff67341a79312ce5a884f467c
Source dataset
uspto-grants-2011_12
Patent number
US08084469B2

Reaction notes

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