Reaction #968

Reaction equation

3-cyanomethyl-1-benzhydryl azetidine

LiAlH4

hydride

→

title compound

Yield 87.0%

3-aminoethyl-1-benzhydryl azetidine

Yield 87.0%

Solvents

THF

Conditions

Workup

1. 1
   TemperatureThe reaction mixture was refluxed for 4 h
2. 2
   Filtrationthe gelatinous mixture was filtered
3. 3
   Washthe filter cake was washed repeatedly with THF
4. 4
   OtherThe solvent was evaporated
5. 5
   workup.DISSOLUTIONthe residue was dissolved in diethyl ether
6. 6
   Washwashed with brine
7. 7
   Dryingdried with Na2SO4
8. 8
   OtherEvaporation of the solvent

Procedure

5.7 g (21.7 mmol) of 3-cyanomethyl-1-benzhydryl azetidine was added slowly to a suspension of 2.9 g (76.0 mmol) of LiAlH4 in 80 mL of dry THF at roomtemperature. The reaction mixture was refluxed for 4 h. Excess hydride reagent was hydrolyzed by careful addition, with cooling, of NH4 Cl(aq), the gelatinous mixture was filtered and the filter cake was washed repeatedly with THF. The solvent was evaporated, the residue was dissolved in diethyl ether, washed with brine and dried with Na2SO4. Evaporation of the solvent gave 5.0 g (87%) of the title compound.

Source