Method for producing N,N-bis(pyridin-2ylmethyl)-1,1-bis(pyridin-2-yl)-1-aminoalkane compounds and metal complex salts containing these compounds
View Patent ↗The invention relates to a method for producing the compositions cited in the title. According to this method: dipyridyl ketone is reacted with hydroxylamine; the oxime obtained thereby is reduced without intermediate isolation to form 1,1-di-(2-pyridyl)-methylamine, and; this amine is firstly reacted with 1 to 1.5 molar equivalent of picolyl chloride and then with another 1 to 1.5 molar equivalent of picolyl chloride to form the amine of formula (1). This amine is purified via the tetrafluoroborate salt and subsequently alkylated with an alkyl iodide. This method represents an improvement with regard to prior art methods for producing these compounds.
1. A process for preparing a N,N-bis(pyridin-2-ylmethyl)-1,1-bis(pyridin-2-yl)-1-aminoalkane compound of formula 1, or a transition metal complex salt thereof as ligand,
where R 1 is C 1 -C 6 alkyl, phenyl or benzyl, said process comprising:
1) reacting dipyridyl ketone with hydroxylamine and reducing the resulting oxime, without isolating it, to provide an amine of formula 2
2) alkylating the amine of formula 2 first with 1 to 1.5 mole equivalents of picolyl chloride and then with a further 1 to 1.5 mole equivalents of picolyl chloride, to provide an amine of formula 3
3) converting the amine of formula 3 into a fluoroborate salt by addition of HBF 4 , and then liberating the amine of formula 3 from the fluoroborate salt by addition of a base, and
4) alkylating the amine of formula 3 with an alkyl halide of the formula
R 1 -hal
to provide the compound of formula (1), and, optionally,
5) converting the compound of formula (1) into the transition metal complex salt, by further reacting the compound of formula (1) with a transition metal salt.
2. The process of claim 1 , wherein R 1 is methyl.
3. The process of claim 1 , wherein the compound of formula (1) is reacted with the transition metal salt to provide the transition metal complex salt of the compound of formula (1) as ligand.