Reaction #945

Reaction equation

benzaldehyde

product

Ethyl 2-aminobutyrate hydrochloride

magnesium sulphate

triethylamine

→

desired product

Yield 88.9%

Ethyl 2-benzylideneaminobutyrate

Yield 88.9%

Solvents

dichloromethane

Conditions

Workup

1. 1
   Filtrationthen filtered
2. 2
   ConcentrationThe filtrate was concentrated
3. 3
   Othertriturated in diethyl ether
4. 4
   Filtrationfiltered
5. 5
   Concentrationconcentrated

Procedure

A solution of the product from step (a) (149.6 g), magnesium sulphate (74.3 g), and triethylamine (246 ml) in dichloromethane (1500 ml) was stirred at room temperature under nitrogen and benzaldehyde (94.9 g, Aldrich) was added dropwise. The mixture was stirred at room temperature for 3 hours then filtered. The filtrate was concentrated, triturated in diethyl ether, filtered and concentrated to yield the desired product as a yellow oil (174 g). 1H NMR consistent with the proposed structure.

Source