Synthesis and configuration of trans-1-amino-4-benzyl-2,6-dimethylpiperazine as an intermediate of semi-synthetic rifamycins |
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Authors: | Giorgio Cignarella Gian Gualberto Gallo |
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Abstract: | The synthesis of trans-1-amino-4-benzyl-2,6-dimethylpiperazine (1b), trans-4-benzyl-2,6-dimethylpiperazine (VIIb) and trans-2,6-dimethylpiperazine (IIb) are described, by condensation of N-benzyl-1,2-propanediamine with α-bromopropionate and successive thermal cyclization and reduction with lithium aluminum hydride. The assignment of the cis, trans configuration to the isomers was based on a thorough examination of the ring proton nmr signals of the two isomers of 4-benzyl-2,6-dimethylpiperazine (VIIa and VIIb) interpreted in terms of conformational considerations. |
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