Water → 2-(1-Benzylpyrrolidin-3-yl)acetonitrile

HRID 1450710

Reaction equation

HRID 1450710 reaction equation
[CH2:1]([N:8]1[CH2:12][CH2:11][CH:10]([CH2:13]Cl)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C-:15]#[N:16].[Na+].O>CS(C)=O>[CH2:1]([N:8]1[CH2:12][CH2:11][CH:10]([CH2:13][C:15]#[N:16])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 8929Sodium CyanideHCID 123645181-Benzyl-3-(chloromethyl)pyrrolidine

Product 1

HCID 123645192-(1-Benzylpyrrolidin-3-yl)acetonitrileYield 92%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
60 °C

Procedure

16.8 g (0.08 mole) (3RS)-1-benzyl-3-chloromethyl pyrrolidine and 5.88 g (0.12 mole) of sodium cyanide was dissolved in 250 ml dimethyl sulfoxide. The mixture was stirred at 60° C. for two days and at room temperature for one week. Water was added and the mixture was extracted three times with ethyl acetate. The combined organic layer was washed with brine, dried (Na2SO4), filtered and evaporated to yield 14.7 g (92%) of the product.

Workup

  1. extractionthe mixture was extracted three times with ethyl acetate
  2. washThe combined organic layer was washed with brine
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-dc34aa2ab9db4a0e84ef10a312e3d667
Source dataset
uspto-grants-1997_02
Patent number
US05602253

Linked notes

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