N-Benzylidene-N-phenethylamine is an aldimine (an imine which is derived from an aldehyde). It's found naturally in cocoa powders.
Benzaldehyde (1.6 mL, 16 mmol, 1 eq) is added slowly to a stirring mixture of diethyl ether (4 mL) and phenylethylamine (2 mL, 16 mmol, 1 eq). The reaction is left to stir at room temperature for 4 hours. The reaction mixture is dried over magnesium sulfate, filtered and then concentrated to give a yellow liquid, which crystallizes on standing giving a yield of 2.7 g (81%) N-benzylidene-N-phenethylamine. Reaction was confirmed by H-NMR.
Aldehyde Condensation Reaction in Cocoa
The quantity of N-benzylidene-N-phenethylamine found in dry cocoa powder increases as the dry cocoa powder ages.
N-Benzylidene-N-phenethylamine occurs naturally as a condensation reaction between the alkaloid phenylethylamine and the aldehyde benzaldehyde in dry cocoa powder. This condensation reaction between phenylethylamine and benzaldehyde produces water as a byproduct.
|Condensation Reactants||Condensation End Products|
Synonyms: N-phenylmethyl-N-phenylmethylene amine; N-phenethyl-1-phenylmethanimine
PubChem Compound ID: 576350
Molecular Weight: 209.2863 [g/mol]
Molecular Formula: C15H15N
IUPAC Name: 1-phenyl-N-(2-phenylethyl)methanimine
Canonical SMILES: C1=CC=C(C=C1)CCN=CC2=CC=CC=C2
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