Antineoplastic Agents. XVIII. N-(2-Haloethyl)Benzylamines

A series of N-benzyl-N-(2-haloethyl)amines have been synthesized for comparison of possible antineoplastic properties with those of the corresponding N-bis(2-chloroethyl)amines. Conversion of 3, 4-dichlorobenzoylaziridine (II) with HC1 or HBr to, respectively, amides Ilia and Mb followed by a diborane reduction sequence yielding amines IYa and IYb outlines the synthetic methods employed. Several N-2-iodoethylamides of the type illustrated by structure IIIc were prepared from the corresponding aziridine amide employing HI or from a N-2-ehloroethyiamide precursor using Xal in acetone. Reaction between the N-2-iodoethylamides and diborane (in tetrahydrofuran) at approximately 60° for 2 hr or at room temperature (overnight) was shown to cause virtually complete hydrogenolysis of the C-I bond. Presently available biological results indicate the N-(2-chloroethy 1 )-benzylamines to be considerably less active than the corresponding X-bis(2-chloroethyl)benzylamines.