55556-91-7

Usage

Uses

Used in Pharmaceutical Synthesis:
1-Nitroso-4-piperidone is used as a key intermediate in the synthesis of 1-Methyl-4-piperidone-2,2,6,6-d4 (M325932), which is a compound with potential applications in the pharmaceutical industry. The synthesis of M325932 involves the use of 1-nitroso-4-piperidone as a starting material, highlighting its importance in the development of new drugs and therapeutic agents.
In the synthesis process, 1-nitroso-4-piperidone undergoes various chemical reactions to form the desired product, M325932. 1-nitroso-4-piperidone may have potential applications in the treatment of certain medical conditions or may be used as a precursor for further chemical modifications to create other valuable compounds.

Safety Profile

Questionable carcinogen withexperimental tumorigenic data. Mutation data reported.Many N-nitroso compounds are carcinogens. Whenheated to decomposition it emits toxic fumes of NOx. Seealso N-NITROSO COMPOUNDS and KETONES

InChI:InChI=1/C5H8N2O2/c8-5-1-3-7(6-9)4-2-5/h1-4H2

Upstream product

• 41661-47-6 piperidin-4-one 
• 298228-66-7 1,4,4-trinitropiperidine 
• 100-75-4 N-nitrosopiperidine 

Relevant academic research and scientific papers

A comparison of the thermal decomposition of nitramines and difluoramines

The decomposition rates and product distributions of a number of nitro- and difluoramino-substituted six-membered rings were compared: nitrocyclohexane (I); 1,1-dinitro-cyclohexane (II); 1,1,4,4-tetranitrocyclohexane (III), 1,1,4,4-tetrakis(difluoramino)cyclohexane (IV); 1,4-dinitropiperazine (V); 1,4,4-trinitropiperidine (VI), and 4,4-bis(difluoramino)-1-nitropiperidine (VII). The study suggested the following order for susceptibility to decomposition: N-NO2 > C-(NO2)2 > C-(NF2)2 The difference in bond energies among the compounds is small. Geminal bis(difluoramino) compounds appeared to be somewhat more stable than the corresponding gem-dinitro compounds though they released more heat during decomposition. Where a nitramine functionality was present, the nitroso analogue was observed as a major decomposition product. The decomposition of gem-bis(difluoramino) and gem-dinitro compounds exhibited similarities. Both experienced loss of one geminal NX2 group followed by the rearrangement of the remaining NX2. Where X was oxygen, loss of the initial nitro by homolysis was favored; rearrangement of the remaining nitro followed by homolysis of NO resulted in a C=O bond. Where X was fluorine, the initial difluoramino may have been lost as HNF2. The remaining difluoramino reacted by losing fluorine, leaving C=NF or by losing HNF, resulting in =C-F; the latter was mainly observed.

Oxidation of N-Nitrosodibenzylamine and Related Compounds by Metalloporphyrin-catalysed Model Systems for the Cytochrome P450 Dependent Mono-oxygenases

N-Nitrosodibenzylamine has been oxidised to benzaldehyde and benzyl alcohol by iodosylbenzene, 3-chloroperoxybenzoic acid and t-butyl hydroperoxide catalysed by tetraphenylporphyrinato-iron(III) chloride or -manganese(III) chloride.The influence of reaction conditions on the product yields and distribution have been studied.Kinetic isotope effects have been measured with deuteriated N-nitrosodibenzylamines for inter- and intra-molecular competition for the oxidants.The evidence presented is in favour of the iodosylbenzene and t-butyl hydroperoxide oxidations being initiated by hydrogen-atom abstraction by the oxidant from the α-hydrogen of the benzyl group.However, oxidations by the peroxy acid systems may proceed by an initial electron transfer.The reactions of N-nitrosodimethylamine and N-nitrosopiperidine with the metalloporphyrin-catalysed systems show that these substrates are surprisingly unreactive towards oxidation.