Reaction #962

Reaction equation

(3RS)-1-benzyl-3-chloromethyl pyrrolidine

sodium cyanide

Water

→

product

Yield 92.0%

(3RS)-1-benzyl-3-cyanomethyl pyrrolidine

Yield 92.0%

Solvents

dimethyl sulfoxide

Conditions

Workup

1. 1
   Extractionthe mixture was extracted three times with ethyl acetate
2. 2
   WashThe combined organic layer was washed with brine
3. 3
   Dryingdried (Na2SO4)
4. 4
   Filtrationfiltered
5. 5
   Otherevaporated

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.

Source