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

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

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.