Water → N-(10-Undecenyl)glutarimide

HRID 1954121Notes

Reaction equation

HRID 1954121 reaction equation
[H-].[Na+].[C:3]1(=[O:10])[NH:8][C:7](=[O:9])[CH2:6][CH2:5][CH2:4]1.Br[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH:21]=[CH2:22].O>CS(C)=O>[CH2:22]([N:8]1[C:7](=[O:9])[CH2:6][CH2:5][CH2:4][C:3]1=[O:10])[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH:13]=[CH2:12]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 70726GlutarimideHCID 28414811-Bromo-1-undecene

Product 1

HCID 23295900N-(10-Undecenyl)glutarimideYield 58.6%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

This example illustrates a synthesis of N-(11,10-Oxidoundecyl)glutarimide (inventive compound no. 1611). Sodium hydride (95%) (168 mg, 7 mmol) was added to a solution of glutarimide (565.6 mg, 5 mmol) in dimethyl sulfoxide (15 mL). After 20 minutes of stirring, 1-bromundec-10-ene (1.165 g, 5 mmol) was added and stirred for 12 hours at room temperature. The reaction mixture was then poured into a separatory funnel containing 100 mL of water and extracted with dichlormethane (5×75 mL). The organic extracts were combined, washed with water (50 mL) and brine (50 mL), dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The crude product obtained was further purified by flash chromatography over silica gel using 20% ethyl acetate/hexane eluant to yield 0.777 g (58.6% yield) N-(10-Undecenyl)glutarimide (inventive compound no. 1610).

Workup

  1. stirringstirred for 12 hours at room temperature
  2. additionThe reaction mixture was then poured into a separatory funnel
  3. extractionextracted with dichlormethane (5×75 mL)
  4. washwashed with water (50 mL) and brine (50 mL)
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe crude product obtained
  8. customwas further purified by flash chromatography over silica gel using 20% ethyl acetate/hexane eluant

Sources & evidence

ORD record
ord-f5df4faf0b2547c98226345a038a09f1
Source dataset
uspto-grants-2000_09
Patent number
US06121270

Reaction notes

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