Magnesium → HCID 70874708, compound

HRID 2172248Notes

Reaction equation

HRID 2172248 reaction equation
[Mg].[CH3:2][C:3]([N:23]1[CH2:28][CH2:27][N:26](S(C2C=CC(C)=CC=2)(=O)=O)[CH2:25][CH2:24]1)([C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][CH:14]=2)=[CH:7][CH:6]=1)[CH3:4]>CO>[CH3:4][C:3]([N:23]1[CH2:24][CH2:25][NH:26][CH2:27][CH2:28]1)([C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:12][C:13]2[CH:14]=[CH:15][C:16]([C:19]([F:20])([F:21])[F:22])=[CH:17][CH:18]=2)=[CH:7][CH:6]=1)[CH3:2]

Participants

4

Reactant 2

HCID 5462224Magnesium2×HCID 86709392HCID 86709392, compound

Product 1

HCID 70874708HCID 70874708, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

Magnesium (1.83 g, 75.0 mmol) was added to a methanol solution (50 ml) of 1-{1-methyl-1-[4-(4-trifluoromethylbenzyloxy)phenyl]ethyl}-4-(toluene-4-sulfonyl]piperazine (2.67 g, 5.0 mmol) and stirred at 60° C. After hours, magnesium (0.61 g, 25.1 mmol) was added thereto and further stirred. After 1 hour, heating was stopped and the solvent was distilled off. Ice and 10% hydrochloric acid (100 ml) were added to the residue and stirred. Ethyl acetate was added and further stirred. The mixture was separated into layers, and the water layer was made basic using a 25% sodium hydroxide aqueous solution. Ethyl acetate was added to the mixture, followed by stirring. The mixture was filtered through Celite to remove the insoluble matter. The filtrate was subjected to extraction with ethyl acetate. The organic layer was dried over sodium sulfate. After removing the desiccant by filtration, the solvent was distilled off to afford the title compound as a slightly yellow oil (1.05 g, 55%).

Workup

  1. waitAfter hours
  2. temperatureheating
  3. distillationthe solvent was distilled off
  4. additionIce and 10% hydrochloric acid (100 ml) were added to the residue
  5. stirringstirred
  6. additionEthyl acetate was added
  7. stirringfurther stirred
  8. customThe mixture was separated into layers
  9. additionEthyl acetate was added to the mixture
  10. stirringby stirring
  11. filtrationThe mixture was filtered through Celite
  12. customto remove the insoluble matter
  13. extractionThe filtrate was subjected to extraction with ethyl acetate
  14. dry with materialThe organic layer was dried over sodium sulfate
  15. customAfter removing the
  16. filtrationdesiccant by filtration
  17. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-6352c6238f524a3cb21859e4e6b1f1d2
Source dataset
uspto-grants-2015_06
Patent number
US09051333B2

Reaction notes

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