The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《The action of piperidine on the bromine derivatives of α,β-unsaturated esters. I. Mechanism of the reactions》. Authors are Moureu, H.; Chovin, P.; Garein, M.; Venttrillard, J..The article about the compound:1-Piperidineacetic Acidcas:3235-67-4,SMILESS:OC(=O)CN1CCCCC1).Category: isoxazole. Through the article, more information about this compound (cas:3235-67-4) is conveyed.
Piperidine (I) (1 mole) added to a α,β-dibromoalkanoic acid ester extracts 1 mole HBr. In the cinnamic acid series, hydrolysis of PhCHBrCHBrCO2Me gives 2 α-Br isomers, the allo and the ordinary. The best exptl. argument in favor of the α,β-substitution of the α,β-dipiperidino-2-alkenoic acid ester (II) is the formation, in the cinnamic acid series, of 2 distinct isomeric dipiperidino esters, m. 77° and 127°. In the MeCH:CHCO2H hydrolysis of the MeCHBrCHBrCO2Et gives 2 isomers, iso and ordinary. I (3 moles) added to MeCH:CBrCO2Et gives II. Et α-bromocrotonate, b16 81-2°, and Et α-bromoisocrotonate, b19 80-1°, are obtained by the direct esterification of α-bromocrotonic and α-isocrotonic acids, resp. The action of 3 moles I on each of these 2 isomers produces the dipiperidino compounds, which on hydrolysis with 2N H2SO4 yield MeCH2COCO2H, 2 moles piperidine, and a primary alc. This, and an accessory reaction, in which the hydrolytic products formed are free piperidine the aldehyde RCHO (BzH or AcH) and piperidinoacetic acid, can be, considered as supplementary proof of the α,β structure of the diamine derivatives
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Reference:
Isoxazole – Wikipedia,
Isoxazole | C3H3NO – PubChem