Dimethyl Sulfoxide → 4-Benzyl-2-morpholineacetonitrile

HRID 1608215Notes

Reaction equation

HRID 1608215 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][O:11][CH:10]([CH2:14]Cl)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C-:16]#[N:17].[K+].CS(C)=O>O.[I-].[K+]>[CH2:1]([N:8]1[CH2:13][CH2:12][O:11][CH:10]([CH2:14][C:16]#[N:17])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 679Dimethyl SulfoxideHCID 9032Potassium CyanideHCID 28015624-Benzyl-2-(chloromethyl)morpholine

Product 1

HCID 32484164-Benzyl-2-morpholineacetonitrileYield 92.8%

Reagents, catalysts & solvents 2

HCID 4875Potassium IodideCatalystHCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 4-benzyl-2-chloromethylmorpholine (22.5 g), potassium cyanide (13 g), potassium iodide (1 g), and dimethyl sulfoxide (40 ml) is heated with stirring at 120° C. for 5 hours. The reaction mixture is cooled, diluted with water, and extracted with diethyl ether. The organic layer is washed with water, dried over sodium sulfate, and evaporated to give the title compound (20 g) as an oil.

Workup

  1. temperatureis heated
  2. temperatureThe reaction mixture is cooled
  3. extractionextracted with diethyl ether
  4. washThe organic layer is washed with water
  5. dry with materialdried over sodium sulfate
  6. customevaporated

Sources & evidence

ORD record
ord-41e789ef8c1144c2a2c531ef8c2002fc
Source dataset
uspto-grants-1989_09
Patent number
US04870074

Reaction notes

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