Direct N1-monosubstitution of piperazine

Result code in IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00216224%3A14310%2F13%3A00074526" target="_blank" >RIV/00216224:14310/13:00074526 - isvavai.cz</a>

Alternative codes found

RIV/00216224:14310/14:00088826

Result on the web

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DOI - Digital Object Identifier

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Result language

čeština

Original language name

Direct N1-monosubstitution of piperazine

Original language description

We report new methods for the efficient direct N1-monosubstitution of piperazine based on the reaction of piperazine-1-ium cation with different electrophilic agents optionally under catalysis by various metal ions supported on weakly acidic cation-exchanger resin. Starting piperazine-1-ium was generated in situ from piperazine in acetic acid solution or by chemi-sorption of piperazine on weakly acidic cation-exchanger resin (i. e. solid phase synthesis with ionically bonded substrate). These two methods were used for reaction with electrophilic reagents such as acyl chlorides, anhydrides, sulfonyl chlorides, carbamoyl chlorides, for example. For aza-Michael additions of piperazine-1-ium cation to compounds with an activated multiple carbon-carbon bond(derivatives of acrylic, propiolic and acetylenedicarboxylic acid) this cation was generated in methanol solution by mixing of piperazine with piperazine-1,4-diium dichloride in various proportions.

Czech name

Direct N1-monosubstitution of piperazine

Czech description

We report new methods for the efficient direct N1-monosubstitution of piperazine based on the reaction of piperazine-1-ium cation with different electrophilic agents optionally under catalysis by various metal ions supported on weakly acidic cation-exchanger resin. Starting piperazine-1-ium was generated in situ from piperazine in acetic acid solution or by chemi-sorption of piperazine on weakly acidic cation-exchanger resin (i. e. solid phase synthesis with ionically bonded substrate). These two methods were used for reaction with electrophilic reagents such as acyl chlorides, anhydrides, sulfonyl chlorides, carbamoyl chlorides, for example. For aza-Michael additions of piperazine-1-ium cation to compounds with an activated multiple carbon-carbon bond(derivatives of acrylic, propiolic and acetylenedicarboxylic acid) this cation was generated in methanol solution by mixing of piperazine with piperazine-1,4-diium dichloride in various proportions.

Type

O - Miscellaneous

CEP classification

CC - Organic chemistry

OECD FORD branch

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Project

<a href="/en/project/2A-1TP1%2F090" target="_blank" >2A-1TP1/090: New catalysts and reagents for sustainable green syntheses and combinatorial syntheses</a><br>

Continuities

P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)

Publication year

2013

Confidentiality

S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů