Water → HCID 23295942, compound

HRID 1954125Notes

Reaction equation

HRID 1954125 reaction equation
[H-].[Na+].[NH:3]1[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1.Br[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH:19]=[CH2:20].O>CS(C)=O>[CH2:20]([N:3]1[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1)[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH:11]=[CH2:10]

Participants

6

Reactant 4

HCID 962WaterHCID 8082PiperidineHCID 24758Sodium hydrideHCID 28414811-Bromo-1-undecene

Product 1

HCID 23295942HCID 23295942, compoundYield 262.8%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

This example illustrates a synthesis of N-(9,10-Oxidodecyl)piperidine (inventive compound no. 1619). Sodium hydride (95%) (864 mg, 36 mmol) was added to a solution of piperidine (2.554 g, 30 mmol) in dimethyl sulfoxide (75 mL). After 20 minutes of stirring, 1-bromundec-10-ene (6.99 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 5% methanol/dichloromethane eluant to yield 3.12 g (44% yield) N-(10-undecenyl)piperidine (inventive compound no. 1615).

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 5% methanol/dichloromethane eluant

Sources & evidence

ORD record
ord-9acd3c68c5714d10b7aa1945289fe687
Source dataset
uspto-grants-2000_09
Patent number
US06121270

Reaction notes

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