The use of bis(aminol) ethers derived from aliphatic primary amines in the synthesis of secondary and tertiary amines

A series of bis(aminol) ethers were prepared from primary aliphatic amines and benzylamine together with formaldehyde and either ethanol or methanol; they were reacted with electrophiles to give N-alkyl-N-alkoxymethyl-methyleneiminium salts which gave mixtures of secondary and tertiary amines in reactions with electron rich aromatic compounds: sequential reactions with two different nucleophiles gave the expected tertiary amines.