Dibenzyl-2-trifluoromethylpiperazine → 2-(Trifluoromethyl)piperazine

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Reaction Steps

2-Trifluoromethylpiperazine (Jenneskens et al., Ref 88c) was prepared through a four step route (Scheme 56). Using Lewis acid TiCl4, N,N′-dibenzylethylenediamine reacted with trifluoropyruvates to afford the hemiacetal, which was reduced at room temperature by Et3SiH in TFA to afford the lactam. LiAlH4 treatment then reduced the lactam to 1,4-dibenzyl-2-trifluoromethylpiperazine. Finally, hydrogenation of the dibenzyl-2-trifluoromethylpiperazine in HOAc gave the desired product, 2-trifluoromethylpiperazine.

Provenance & Evidence