Sodium Cyanide → 2-(1-Benzylpyrrolidin-2-yl)acetonitrile

HRID 1253498Notes

Reaction equation

HRID 1253498 reaction equation
[CH2:1]([N:8]1[CH2:12][CH2:11][CH2:10][CH:9]1[CH2:13]Cl)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C-:15]#[N:16].[Na+]>CN(C)C=O.O>[CH2:1]([N:8]1[CH2:12][CH2:11][CH2:10][CH:9]1[CH2:13][C:15]#[N:16])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 8929Sodium CyanideHCID 30426421-Benzyl-2-(chloromethyl)pyrrolidine

Product 1

HCID 226628942-(1-Benzylpyrrolidin-2-yl)acetonitrile

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6228DimethylformamideSolvent

Procedure

Into a 3,000 ml 3-necked roundbottom flask, was placed a solution of 1-benzyl-2-(chloromethyl)pyrrolidine (150. g, 714 mmol) in N,N-dimethylformamide (1,500 ml). This was followed by the addition of a solution of NaCN (54.2 g, 834 mmol) in water (300 ml). The resulting solution was heated to reflux for 2 hours. After cooling to ambient temperature, the solution was dissolved in 6,000 ml of water. The resulting solution was extracted with ethyl acetate (3×3,000 ml) and the combined organic layers were dried over sodium sulfate, filtered and concentrated. The residue was purified by flash column chromatography (ethylacetate/petroleum ether gradient) to afford 2-(1-benzylpyrrolidin-2-yl)acetonitrile.

Workup

  1. customInto a 3,000 ml 3-necked roundbottom flask, was placed
  2. temperatureThe resulting solution was heated
  3. temperatureto reflux for 2 hours
  4. extractionThe resulting solution was extracted with ethyl acetate (3×3,000 ml)
  5. dry with materialthe combined organic layers were dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by flash column chromatography (ethylacetate/petroleum ether gradient)

Sources & evidence

ORD record
ord-c9a9922ad0944505be37a0ac4823644a
Source dataset
uspto-grants-2013_06
Patent number
US08455477B2

Reaction notes

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