Water → HCID 23081324, compound

HRID 856118Notes

Reaction equation

HRID 856118 reaction equation
[I-].[CH3:2][S+](C)(C)=O.[H-].[Na+].[O:9]=[C:10]([CH3:26])[CH2:11][CH2:12][N:13]1[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15][CH2:14]1.O>CS(C)=O>[CH3:26][C:10]1([CH2:11][CH2:12][N:13]2[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15][CH2:14]2)[CH2:2][O:9]1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 23081416HCID 23081416, compound

Product 1

HCID 23081324HCID 23081324, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

Trimethylsulfoxonium iodide (7.8 g, 35 mmol) was gradually added to a suspension of sodium hydride (1.2 g, 35 mmol) in DMSO (120 ml), under a nitrogen atmosphere, and the mixture was stirred at room temperature for 2 hours. To which a solution of tert-butyl 4-(3-oxobutyl)piperazine-1-carboxylate (6.1 g, 23.8 mmol) in DMSO (10 ml) was gradually added dropwise, and the mixture was stirred at room temperature for 1.5 hours, and then at 50 to 60° C. for 1.5 hours. The reaction solution was allowed to return to room temperature, poured into iced water, and extracted with ethyl acetate three times. The extracts were combined, washed with water three times and then washed with a saturated saline solution, and dried over sodium sulfate. After filtration, the filtrate was concentrated under a reduced pressure to afford tert-butyl 4-[2-(2-methyl-2-oxiranyl)ethyl]piperazine-1-carboxylate (5.6 g, 87%) as a light yellow oil.

Workup

  1. stirringthe mixture was stirred at room temperature for 1.5 hours
  2. waitat 50 to 60° C. for 1.5 hours
  3. customto return to room temperature
  4. extractionextracted with ethyl acetate three times
  5. washwashed with water three times
  6. washwashed with a saturated saline solution
  7. dry with materialdried over sodium sulfate
  8. filtrationAfter filtration
  9. concentrationthe filtrate was concentrated under a reduced pressure

Sources & evidence

ORD record
ord-a350af491f2b4256a3d44b54ab6981c4
Source dataset
uspto-grants-2007_08
Patent number
US07262212B2

Reaction notes

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