Water → HCID 69083181, compound

HRID 594392Notes

Reaction equation

HRID 594392 reaction equation
[NH:1]1[C:6](=[O:7])[CH2:5][CH2:4][CH2:3][C:2]1=[O:8].[OH-].[K+].Br[CH2:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][C:20]([F:23])([F:22])[F:21])=[CH:15][CH:14]=1.O>CN(C=O)C>[F:21][C:20]([F:22])([F:23])[O:19][C:16]1[CH:17]=[CH:18][C:13]([CH2:12][N:1]2[C:6](=[O:7])[CH2:5][CH2:4][CH2:3][C:2]2=[O:8])=[CH:14][CH:15]=1

Participants

6

Reactant 4

HCID 962WaterHCID 14797Potassium HydroxideHCID 70726GlutarimideHCID 1427851-(Bromomethyl)-4-(trifluoromethoxy)benzene

Product 1

HCID 69083181HCID 69083181, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A cooled (0° C.) mixture of commercially available piperidine-2,6-dione (400 mg; 3.46 mmol; 1.0 equiv.) and KOH (213 mg; 3.81 mmol; 1.1 equiv.) in anh. DMF (3.5 ml) was stirred, under nitrogen, for 30 min., and was then treated with a solution of commercially available 1-(bromomethyl)-4-(trifluoromethoxy)benzene (956 mg; 3.63 mmol; 1.05 equiv.) in anh. DMF (1 ml). The resulting mixture was further stirred at rt, under nitrogen, for 3 days. Water was added, and the mixture was extracted with Et2O (3×). The mixed organic layers were washed successively with 2 M aq. NaOH, aq. sat. NH4Cl, and brine, dried over anh. MgSO4, filtered, and concentrated to dryness under reduced pressure affording 1-(4-(trifluoromethoxy)benzyl)piperidine-2,6-dione as a colorless oil. LC-MS (conditions E): tR=0.67 min.; no ionisation.

Workup

  1. temperatureA cooled
  2. stirringThe resulting mixture was further stirred at rt, under nitrogen, for 3 days
  3. extractionthe mixture was extracted with Et2O (3×)
  4. washThe mixed organic layers were washed successively with 2 M aq. NaOH, aq. sat. NH4Cl, and brine
  5. dry with materialdried over anh. MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-7fab1df76ad249ab9075ad16751e83c0
Source dataset
uspto-grants-2016_01
Patent number
US09242970B2

Reaction notes

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