Benzylamine → HCID 3937474, compound

Participants

Reaction Conditions

Reaction Steps

113 ml (818 mmol) of triethylamine were added to 96.4 g (600 mmol) of cinnamyl chloride in 800 ml of tetrahydrofuran, the mixture was heated to 60° C., and then 65.4 ml (600 mmol) of benzylamine were added dropwise. The mixture was refluxed for 3 h and then stirred at room temperature for 15 h. After concentration under water pump vacuum, the contents of the flask were partitioned between methyl t-butyl ether and water (pH=10). The organic phase was washed twice with water, dried with sodium sulfate and concentrated. The crude product (109 g) composed of mono- and bisadduct was dissolved in 400 ml of acetone, a solution of 48 g (413 mmol) of maleic acid in 250 ml of acetone was added while stirring and, after cooling, the precipitated solid was filtered off with suction. After washing with acetone, 60.0 g (30%) of N-cinnamylbenzylamine were isolated as maleate, melting point 169°-170° C.

Provenance & Evidence