Development of a Scalable Synthesis of Oligomeric Piperidine‑N‑O‑alkyl Ethers

Development of a Scalable Synthesis of Oligomeric Piperidine‑N‑O‑alkyl Ethers

An efficient two-step manufacturing process for a novel polypiperidine-N-O-alkyl ether was developed. Starting from an oligomeric 2,2,6,6-tetramethylpiperidine derivative, oxidation by hydrogen peroxide yielded a polynitroxide radical. Subsequently, the intermediate was reacted with alkyl radicals t...

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Bibliographic Details
Published in:Organic process research & development Vol. 18; no. 12; pp. 1843 - 1849
Main Authors: Cote, Everett, Chafin, Laura, DiFazio, Mike, Robbins, Jim, Kotrola, Joe, Nocentini, Tiziano, Schoening, Kai-Uwe
Format: Journal Article
Language:English
Published: American Chemical Society 19-12-2014
Online Access:Get full text
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Summary:An efficient two-step manufacturing process for a novel polypiperidine-N-O-alkyl ether was developed. Starting from an oligomeric 2,2,6,6-tetramethylpiperidine derivative, oxidation by hydrogen peroxide yielded a polynitroxide radical. Subsequently, the intermediate was reacted with alkyl radicals to provide the corresponding hydroxylamine O-alkyl ether. The optimized process was amenable to scale-up, and 1 metric ton of the target compound was prepared in high yield as a product-by-process.
ISSN:1083-6160
1520-586X
DOI:10.1021/op500301r