The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Amino acids. I. Synthesis of some tertiary aminoacetic acids》. Authors are Remizov, A. L..The article about the compound:1-Piperidineacetic Acidcas:3235-67-4,SMILESS:OC(=O)CN1CCCCC1).Name: 1-Piperidineacetic Acid. Through the article, more information about this compound (cas:3235-67-4) is conveyed.
It was shown that reaction of ClCH2CO2H with R2NH depends on the basicity of the amine used and on steric factors. Benzylidenecyclohexylamine and MeI gave C6H11NHMe.HCl, m. 178-9°; free amine b62 73°. MeOCH2CH2Cl in MeOH-NH3 in 12 hrs. at 90-5° gave 5% MeOCH2CH2NH2, b. 92-5° (picrate m. 147-9°), 42% (MeOCH2CH2)2NH, b21 67-8°, n20D 1.4211 (picrate m. 112-14°; picrolonate m. 178-9°), and 19% (MeOCH2CH2)3N, b10 100-1°, 1.4330 (picrate m. 65-6°; picrolonate m. 119-20°). Shaking 0.06 mole ClCH2CO2H after neutralization with a paste of BaCO3 with 0.06 mole desired amine in H2O 4 hrs. followed by 20 hrs. at room temperature gave, after final heating on a steam bath to complete the reaction, RR’NCH2CO2H (NRR’ and m.p. given): Me2N, 179-81° (HCl salt m. 190-1°); Et2N, 135-6° (HCl salt m. 126-7°); piperidino, 208-11° (HCl salt m. 217-21°); morpholino, 162-3.5° (HCl salt m. 169-71°); C6H11NMe, 186-7° (HCl salt m. 166-7°); (MeOCH2CH2)2N, 48-9.5° (picrolonate m. 116-17°). These were accompanied by 2-20% RR’N(CH2CO2H)2Cl (same data given): NMe2, decomposed 208-9°; NEt2, decomposed 244-6°; MeNC6H11, decomposed 205-7°. For avoidance of formation of these salts, the secondary amines should be used in excess; alternatively, ClCH2CO2H was neutralized with aqueous NaOH and kept overnight with RR”NH, then heated on a steam bath.
As far as I know, this compound(3235-67-4)Name: 1-Piperidineacetic Acid can be applied in many ways, which is helpful for the development of experiments. Therefore many people are doing relevant researches.
Reference:
Isoxazole – Wikipedia,
Isoxazole | C3H3NO – PubChem