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

Participants

Reaction Conditions

Reaction Steps

S. Gump and E.J. Nikaivitz in Example 3 of U.S. Pat. No. 2,504,977 issued April 25, 1950, show the reaction of 190 g of benzyl chloride with 315 g of N,N-bis(2-hydroxyethyl)amine at 100-125° C. for nine hours followed by addition of sufficient saturated potassium carbonate to neutralize "the formed hydrochlorides" and continued stirring of the mixture for thirty minutes at 90° C. The separated oil in isopropyl ether and ethanol was dried and distilled twice to produce 162 g (54.3% yield) of pure N,N-bis(2-hydroxyethyl)benzylamine. A 97 g portion of N,N-bis(2-hydroxyethyl)benzylamine was converted into 115 g (85.7% yield) of N,N-bis(2-chloroethyl)benzylamine hydrochloride (46.5% yield based on benzyl chloride) by adding dropwise with stirring 120 g of thionyl chloride in chloroform to a cooled (ice bath) chloroform solution of N,N-bis(2-hydroxyethyl)benzylamine, and then isolating the product and converting it to its hydrochloride salt.

Provenance & Evidence