Tetrahydro-methyl-pyridinecarboxylic acid

A bicyclic urea (123) was an unexpected product of the reaction between pyrrolidine and the phenyl ester of 2-cyano-l,4,5,6-tetrahydro-l-pyridinecarboxylic acid (124 R = Ph) the corresponding methyl ester (124 R = Me) reacted, as expected, to give the product of Michael addition (125). ° The better leaving ability of phenoxide vs methoxide presumably tilted the reaction towards the substitution rather than the addition product, although thiols (e.g. PhSH) underwent only the addition reaction. 

Beilstein Handbook Reference) BRN 111256 Guvacine 3-Pyridinecarboxylio acid, 1,2,5,6-tetrahydro- 1,2,5,6-Tetrahydro-3-pyridinecarboxylic acid 1,2,5,6-Tetrahydronicotlnic acid, A pyridine alkaloid derived from betel nuts. Its methyl ester is also called guvacine. Prisms or rods mp = 295 (dec) very soluble in H2O, insoluble in organic solvents. 

RN 70-19-9 MF Ci.HijNOj MW 207.23 EINECS 200-727-5 CN 3-pyridinecarboxylic acid (tetrahydro-2-furanyl)methyl ester... 

Arecaidine (= Arecaine 1,2,5,6-Tetrahydro-1 -methyl-3-pyridinecarboxylic acid) (piperidine)... 

Beilstein Handbook Reference) Arecaidine Areoaine BRN 0112366 Methylguvacine N-Methylguvacine Nicotinic acid, 1,2,5,6-tetrahydro-1-methyl- NSC 76017 3-Pyridinecarboxylic acid, 1,2,5,6-tetrahydro-1-methyl- 1,2,6,6-Tetrahydro-1-methylnioo-tinic acid 1,2,5,6-Tetrahydro-1-methyl-3-pyridine-carboxylic acid. Isolated from betel nuts. Plates or tablets, mp = 232° (dec)insoluble in EtOH, Et20, CeHe, CHCI3, very soluble in H2O. 

Tetrahydro-l-methylnicotinic acid, methyl ester 1,2,5,6-TetrahydrD-1-methyl-3-pyridinecarboxylic acid methyl ester. Used in veterinary medicine as an anthelmintic effective against Cestodes. Oil bp = 209" d n 1.0495 ngP= 1.4302 LDsO (mus sc) = 100 mg/kg. Boetmnger Ingelheim Vetmedica Inc. 

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