Carbon Tetrachloride → Benzenemethanamine, 2,5-dichloro-

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The various benzylamine derivatives used in this study, when not commercially available, were synthesized by the methods shown in FIG. 5. 2,5-Dichlorobenzylamine 64 and 2-chloro-5-iodobenzylamine 65 were prepared from the corresponding benzyl bromides. Compound 60 was prepared from 2-chloro-5-iodotoluene by bromination with N-bromosuccinimide in CCl4. Wilson et al., J. Med. Chem 1989, 32, 1057-1062. 60 and 61 were treated with potassium phthalimide in N,N-dimethylformamide at 60° C. to obtain compounds 62 and 63 as white solids in 95% yield. Deprotection with hydrazine gave 64 and 65 in 80% yield. Treu et al., Molecules 2002, 7, 743-750.

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