Synthesis and configuration of trans‐1‐amino‐4‐benzyl‐2,6‐dimethylpiperazine as an intermediate of semi‐synthetic rifamycins
- 1 December 1974
- journal article
- research article
- Published by Wiley in Journal of Heterocyclic Chemistry
- Vol. 11 (6) , 985-989
- https://doi.org/10.1002/jhet.5570110624
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.Keywords
This publication has 6 references indexed in Scilit:
- Effect of Dimethylbenzyldesmethylrifampicin (DMB) on Chemically Induced Mammary Tumours in RatsNature New Biology, 1973
- INHIBITORS OF THE TRANSCRIBING ENZYMESPublished by Elsevier ,1973
- Inhibitors of the RNA and DNA Dependent Polymerase Activities of RNA Tumour VirusesNature New Biology, 1971
- Proton magnetic resonance studies of cyclic compounds—VITetrahedron, 1968
- 2,6‐Dialkylpiperazines. III. NMR spectra of the geometrical isomers of 4‐phenyl‐2,6‐dimethylpiperazineJournal of Heterocyclic Chemistry, 1965
- 2,6-Dialkylpiperazines. I. Synthesis of cis-2,6-Dimethylpiperazine DerivativesJournal of Medicinal Chemistry, 1964