Benzyl Chloride → 2,2'-((Phenylmethyl)imino)bisethanol

Participants

Reaction Steps

The improvements in the above process aspects of the invention which afford a substantially quantitative yield of N,N-bis(2-chloroethyl)benzylamine, are based in part on modifications which eliminate formation of by-products and in part on a reverse in the order of addition of reactants. One improvement is based on the use of a molar equivalent quantity of sodium carbonate in the reaction of bis(2-hydroxyethyl)amine with benzyl chloride to produce N,N-bis(2-hydroxyethyl)benzyl amine, thereby completely inhibiting formation of the by-products N,N-dibenzyl-N-(2-hydroxyethyl)amine and N-benzyl-N-(2-benzyloxyethyl)-N-(2-hydroxyethyl)amine, which are produced in relatively large quantities (about 16% and 20% respectively) in the absence of said sodium carbonate. Another improvement is based on the addition of N,N-bis(2-hydroxyethyl)benzylamine in toluene solution to slightly more than a two molar excess of thionyl chloride rather than the heretofore reverse addition of thionyl chloride to N,N-bis(2-hydroxyethyl)benzylamine, thereby completely eliminating the formation of N-benzylmorpholine. Another improvement is the azeotropic distillation of the toluene solution of N,N-bis(2-hydroxyethyl)benzylamine to remove the water formed by the reaction, thereby avoiding the use of excess thionyl chloride to ensure completion of reaction in the chlorination step.

Provenance & Evidence