Reaction #63370

Reaction equation

n-pentyl iodide

sodium hydride

1-(4-nitrophenyl)-3-azabicyclo[3.1.1]heptane-2,4-dione

→

1-(4-nitrophenyl)-3-n-pentyl-3-azabicyclo[3.1.1]heptane-2,4-dione

Solvents

N,N-dimethylformamide

N,N-dimethylformamide

N,N-dimethylformamide

Conditions

Workup

1. 1
   workup.ADDITIONare then added dropwise
2. 2
   OtherThe residue is partitioned between ethyl acetate and water
3. 3
   Dryingthe organic phase is dried over magnesium sulphate
4. 4
   Concentrationafter concentration
5. 5
   Otherby evaporation
6. 6
   Otherthe product is obtained

Procedure

0.36 g of sodium hydride is added to a solution of 2.46 g of 1-(4-nitrophenyl)-3-azabicyclo[3.1.1]heptane-2,4-dione in 25 ml of N,N-dimethylformamide and the whole is stirred at room temperature for 30 minutes. 2.96 g of n-pentyl iodide dissolved in 10 ml of N,N-dimethylformamide are then added dropwise thereto. When the reaction is complete, the reaction mixture is freed of N,N-dimethylformamide. The residue is partitioned between ethyl acetate and water, and the organic phase is dried over magnesium sulphate and, after concentration by evaporation, the product is obtained having a melting point of 75°-79°.

Source