Sodium hydride → HCID 23081356, compound

HRID 856123Notes

Reaction equation

HRID 856123 reaction equation
[I-].[CH3:2][S+](C)(C)=O.[H-].[Na+].[F:9][C:10]([F:25])([F:24])[C:11]1[CH:16]=[CH:15][C:14]([N:17]2[CH2:22][CH2:21][C:20](=[O:23])[CH2:19][CH2:18]2)=[CH:13][CH:12]=1>CS(C)=O>[F:25][C:10]([F:9])([F:24])[C:11]1[CH:12]=[CH:13][C:14]([N:17]2[CH2:22][CH2:21][C:20]3([O:23][CH2:2]3)[CH2:19][CH2:18]2)=[CH:15][CH:16]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 212736221-[4-(Trifluoromethyl)phenyl]-4-piperidinone

Product 1

HCID 23081356HCID 23081356, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

Trimethylsulfoxonium iodide (2.00 g, 9.02 mmol) was gradually added to a suspension of sodium hydride (361 mg, 9.02 mmol) in dimethylsulfoxide (30 ml), and the mixture was stirred at room temperature for 1 hour. To which a solution of 1-(4-trifluoromethylphenyl)piperidin-4-one (2.00 g, 8.2 mmol) in DMSO (10 ml) was added, and the mixture was stirred overnight. The reaction mixture was poured into ice water, and extracted with diethyl ether. The extract was washed with brine, dried over sodium sulfate, and then filtered. The residue was purified by silica gel column chromatography (n-hexane/ethyl acetate=5/1) to afford 6-(4-trifluoromethylphenyl)-1-oxa-6-azaspiro[2,5]octane (1.51 g, yield 72%) as a pale yellow crystalline powder.

Workup

  1. stirringthe mixture was stirred overnight
  2. extractionextracted with diethyl ether
  3. washThe extract was washed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customThe residue was purified by silica gel column chromatography (n-hexane/ethyl acetate=5/1)

Sources & evidence

ORD record
ord-c07fc690925043cea36cc23867c54a35
Source dataset
uspto-grants-2007_08
Patent number
US07262212B2

Reaction notes

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