The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《The synthesis of esters of some amino acids having pharmacological importance. I. The synthesis of esters of piperidino carboxylic acids》. Authors are Matkovics, Bela; Foldeak, Sandor; Porszasz, Janos; Sipos, Gyorgy.The article about the compound:1-Piperidineacetic Acidcas:3235-67-4,SMILESS:OC(=O)CN1CCCCC1).Product Details of 3235-67-4. Through the article, more information about this compound (cas:3235-67-4) is conveyed.
RCH2CO2R’ (I), RCH2CH2CO2R’ (II), BzOCH2CH2R (III), and AcOCHMeCH2R (IV) were prepared I were prepared by condensing ClCH2CO2R’ with a secondary amine, II by boiling ClCH2CH2CO2R’ with the amine, and III by the reaction of an amino alc. with BzCl. The following I were obtained (R, R’, b.p.°/mm., m.p. of picrate, m.p. of HCl salt, and m.p. of methiodide are given): piperidino, Me, 69°/5, 115°, 214°, 163-4°; piperidino, Et, 68°/1, 122°, 117-17.5°, 160-60.3°; piperidino, Bu, 100-1°/4, 85°, -, 178°; piperidino, PhCH2, 134-5°/1, 137°, 133°, 91-6°; morpholino, Me, 77°/2, 143°, 150.5°, 147.5°; morpholino, Et, 86-7°/4, 163°, 181°, 132-3°; morpholino, Bu, 105.5-106°/3, -, 127-9°, 95-6°; morpholino, PhCH2, 164-5°/5, 143°, 149°, -; pyrrolidino, Me, 72-3°/8, 104°, -, 153°; pyrrolidino, Et, 59-60°/2, 119.5°, 133-3.5°, -; pyrrolidino, Bu, 81-2°/3, 109.5°, -, -; pyrrolidino, PhCH2, 134-5°/1, 159-60°, 139-40°, 156°. The following II were prepared (data as above): piperidino, Me, 72°/2, 164°, 189°, 147-8°; piperidino, Et, 102-3°/5, 131.5°, 169°, -; piperidino, Bu, 124-5°/6, 108-9°, 164.7°, -; piperidino, PhCH2, 149-50°/1, 113°, 193.5°, -; piperidino, Ph, 114-20°/3, -, 192-5°, -; piperidino, CPh3, 171°/1, -, 214°, -; morpholino, Me, 82°/2, 129°, 203°, 151°; morpholino, Et, 108°/6, 108°, 188-9°, -; morpholino, Bu, 131-2°/6, 150°, 173°, 115°; morpholino, PhCH2, 154°/1, 125°, 189-90°, -; pyrrolidino, Me, 76°/5, 147°, 128°, 166°; pyrrolidino, Et, 85°/6, 114°, 146°, -; pyrrolidino, Bu, 106-8°/5, 97°, 74-5°, 115°; pyrrolidino, PhCH2, 145-6°/3, 102°, 152°, 154°. IV (R =pyrrolidino) (V), b3 75°, picrate m. 111-12°, gave a hygroscopic HCl salt. III (R = piperidino) b2 141°; HCl salt m. 184°; methiodide m. 141.5°. The action of the compounds on blood pressure and on respiration was given. II (R = N-piperidino, R’ = CPh3) and V had strong antinicotinic action. The effect of the piperidino and pyrrolidino propionates was increased by quaternization.
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Reference:
Isoxazole – Wikipedia,
Isoxazole | C3H3NO – PubChem