Sodium hydride → 1-[2-(4-Cyanophenyl)ethyl]piperidin-4-spiro-2'-oxirane

HRID 967763Notes

Reaction equation

HRID 967763 reaction equation
[H-].[Na+].[I-].[CH3:4][S+](C)(C)=O.[C:9]([C:11]1[CH:16]=[CH:15][C:14]([CH2:17][CH2:18][N:19]2[CH2:24][CH2:23][C:22](=[O:25])[CH2:21][CH2:20]2)=[CH:13][CH:12]=1)#[N:10]>CS(C)=O>[C:9]([C:11]1[CH:12]=[CH:13][C:14]([CH2:17][CH2:18][N:19]2[CH2:24][CH2:23][C:22]3([CH2:4][O:25]3)[CH2:21][CH2:20]2)=[CH:15][CH:16]=1)#[N:10]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 222912911-[2-(4-Cyanophenyl)ethyl]piperidin-4-one

Product 1

HCID 858197211-[2-(4-Cyanophenyl)ethyl]piperidin-4-spiro-2'-oxiraneYield 90.1%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

60% sodium hydride (1.89 g) was added to anhydrous dimethylsulfoxide (42 mL) and the mixture was stirred at room temperature for ten minutes under nitrogen atmosphere. After gradually adding trimethylsulfoxonium iodide (10.4 g) to the mixture at 10 to 19° C., the mixture was stirred at 8 to 10° C. for thirty minutes and at room temperature for sixty minutes. An anhydrous dimethylsulfoxide solution (42 mL) of the compound (9.00 g) obtained in Step 2 was added dropwise to the mixture. After stirring the resulting mixture at room temperature for one and half hours, the reaction mixture was poured into an ice water (250 mL) gradually with stirring. The mixture was extracted with ethyl acetate, and the organic layer was combined and washed with water and brine successively. The organic layer was dried over anhydrous sodium sulfate, the solvent was removed under reduced pressure. The residue was crystallized from hexane and collected by filtration to obtain the titled compound (8.61 g) as crystals.

Workup

  1. stirringAfter stirring the resulting mixture at room temperature for one and half hours
  2. stirringwith stirring
  3. extractionThe mixture was extracted with ethyl acetate
  4. washwashed with water and brine successively
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. customthe solvent was removed under reduced pressure
  7. customThe residue was crystallized from hexane
  8. filtrationcollected by filtration

Sources & evidence

ORD record
ord-99ce78b23ad243d9ba4cc18e6b3cd4de
Source dataset
uspto-grants-2005_10
Patent number
US06956046B2

Reaction notes

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