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Substituted and dehydro derivatives of 4-piperidinone are intermediates in alkaloid syntheses. [1] The N-protonated derivative is typically isolated as the hydrate (HO) 2 C(CH 2) 4 NH + 2. [2] It is a List I chemical in the United States as it is a precursor to fentanyl. Fentanyl synthesis using the Gupta method starting from 4-piperidone
Therefore, the product of the reaction is not a bicyclic structure (see tropinone and pseudopelletierine) but a 4-piperidone. The synthesis of tropinone can be seen as a variation of the Petrenko-Kritschenko reaction in which the two aldehyde functions are covalently linked in a single molecule.
A classic named reaction for the synthesis of piperidones is the Petrenko-Kritschenko piperidone synthesis which involves combining an alkyl-1,3-acetonedicarboxylate with benzaldehyde and an amine. [1] This multicomponent reaction is related to the Hantzsch pyridine synthesis.
4-Pyridone is an organic compound with the formula C 5 H 4 NH(O). It is a colorless solid. Preparation. ... 4-Piperidone; Dehydroacetic acid; References
Paul Janssen (founder of Janssen Pharmaceutica) first synthesized fentanyl in 1960 from Benzylfentanyl. [4] The Siegfried method (shown below and published on The Hive) involves reacting N-phenethyl-4-piperidinone with aniline, and then reducing the imine product with sodium borohydride to 4-anilino-N-phenethylpiperidine (ANPP).
Piperidine is also commonly used as a base for the deprotection of Fmoc-amino acids used in solid-phase peptide synthesis. Piperidine is listed as a Table II precursor under the United Nations Convention Against Illicit Traffic in Narcotic Drugs and Psychotropic Substances due to its use (peaking in the 1970s) in the clandestine manufacture of ...
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