Thionyl Chloride → N-benzyl-2-chloro-N-methylethanamine

Participants

Reaction Steps

N-(2-hydroxyethyl)-N-benzyl-methylamine is a known compound and is described in literature (J. Am. Chem. Soc. 76, 4920-23, 1954). The reaction of this compound with thionyl chloride gives N-(2-chloroethyl)-N-benzyl-methylamine in a good yield. This compound can also be prepared by reacting N-benzyl-methylamine with 1-bromo-2-chloroethane, the yields, however, are poor and the dimeric 1,2-bis(N-benzylmethylamino)ethane, which is formed as a by-product, must be separated by chromatography.

Provenance & Evidence