Piperidine-4-carboxylic acid amide

The other method results directly from the piperidine-2-carboxylic acid chloride, which is reacted with 2,6-dimethylaniline. The resulting amide (2.2.8) is further alkylated with butyl bromide to bupivacaine [17-19]. 

The a is L-lysine, as in the case of piperidine, but the f3 is different. The /3 is a-aminoadipic acid 6-semialdehyde. The q> is L-pipecolic acid, which is synthesized in plants from piperideine-6-carboxylic acid. In the case of many other organisms, the obligatory intermedia (q>) is derived from the /3. The

ring structure. The indolizidine nucleus will be formed only in the synthesis of the x- The deep structmal change occms when

Claisen reaction with acetyl or malonyl CoA (Cra/mCoA) and the ring closme process (by amide or imine) to 1-indolizidinone, which is the x- The second obligatory intermedia ( k ) only has the indolizidine nucleus. 

The presence of the propionamide fragment in the stmcture of the anti-inflammatory agent broperamole (125-1) is reminiscent of the heterocycle-based NSAID propionic acids. The activity of this agent may trace back to the acid that would result on hydrolysis of the amide. Tetrazoles are virtually always prepared by reaction of a nitrile with hydrazoic acid or, more commonly, sodium azide in the presence of acid in a reaction very analogous to a 1,3-dipolar cycloaddition. A more recent (and safer) version of the reaction noted later (see losartan, 77-4) uses tributyltin azide. In the case at hand, reaction of the anion of mefa-bromobenzonitrile (125-1) with sodium azide and an acid affords the tetrazole (125-2). Condensation of the anion from that intermediate with ethyl acrylate leads to the product from Michael addition saponiflcation gives the corresponding carboxylic acid (125-3). This is then converted to the acid chloride reaction with piperidine affords broperamole (125-4) [136]. 

Butyl-piperidine-2-carboxylic acid (2,6-dimethyl-phenyl)-amide, C18H28N20, MW 288.44, [2180-92-9]... 

Treatment of polymer films by reactive gases or reactive volatil compounds allows to easily modify polymers containing alcohols, hydroperoxides, carboxylic acids (or acids halides), double bonds or piperidine groups. New functional groups as organic nitrites, nitrates, iodides, acid halides (Cl, F), amides, esters, peresters and nitroxyl radicals can be generated by a single reaction or by combination of two consecutive treatments. The reactions are very efficient on thin films (ca 50-100 pm) and can be controlled by transmission and reflexion 1R spectroscopy. 

Pinacolone, o-(diphenylphosphino)benzoyl-coordination chemistry, 401 Piperidine, IV-hydroxy-metal complexes, 797 pA a values azole ligands, 77 Plant roots amino acids, 962 carboxylic acids, 962 Plastocyanin copper binding site, 557 copper(II) complexes, 772 copper(II) site in, 770 Platinum, dichlorobis(benzonitrile)-IR spectrum, 264 Platinum, cis-dichlorodianunine-antitumor activity, 34, 979 Platinum, ethylenebis(triphenylphosphine)-reactions with 5,6-dimethyl-2,l,3-benzothiadiazole, 194 Platinum blue formation, 265 Platinum complexes acetylacetone reactions, 380 amides, 491 amidines... 

Pyrrolo[2,1 -d][ 1,5]benzothiazepine-6-carboxylic acid (27) was obtained via base-catalyzed cyclization of pyrrole-2-carboxaldehydes 26 and 28, each synthesized by Vilsmeier-Haack formylation of their respective pyrroles 24 and 25, prepared in turn by condensation of 18, respectively, with ethyl bromoacetate and chloroacetonitrile in the presence of sodium ethylate at room temperature. When treated with piperidine in refluxing benzene for 48 hours, 26 and 28 afforded ester 29 and nitrile 31 from which, in an alkaline medium, acid 27 could be obtained. Under similar experimental conditions, acid 27 was also formed from amide 30 (Scheme... 

Methyl-lH-indazol-3-yl)-5-pyridin- 3- yl-thiazole-4-carboxylic acid methyl- (1 -methyl-piperidin-4-yl)-amide 1 H 0 1... 

Sodium cyanoborohydride (10) produces mainly 1,4-dihydropyridines (11) in the reduction of 3,5-di-cyano- and 3,5-diethoxycarbonyl-pyridines, diborane produces more of the 1,2-isomer. With NBH, mixtures of 1,2- and 1,4-dihydro adducts are produced, the latter predominating when carried out in pyridine solution. Nicotinamide (13) in ethanol can be reduced to (8) in moderate yield at 140 C in diglyme the tetrahydropyridine (8) was isolated in admixture with the piperidine (14), presumably via dehydration of the amide. 3-Nitropyridine affords 3-nitropiperidine in moderate yield when reduced in ethanol. The carboxylic acid and halo derivatives of pyridine are generally not reactive toward NBH. 

Kamochi and Kudo have reported the use of the Sml2/THF-H20 system to reduce aromatic carboxylic acids to alcohols (Scheme 50). Furthermore, aromatic esters amides and nitriles were similarly reduced by this system in good yield [104]. As indicated above, reduction of carboxylic acids to primary alcohols is also effective with Sml2 in a THF-H20-NaOH mixture [105]. In contrast, without water these substrates remain unchanged. With the Sml2/THF-H20 system, pyridine was rapidly reduced to piperidine in similar reactions with pyridine derivatives bearing chloro, amino and cyano substituents, these functionalities were partly eliminated to afford pyridine or piperidine [107]. 

Coumarins are known to react with amines to give various products, for example 2,3-dihydrobenzofurans. 3-Bromocoumarin has been shown to give the benzofuran (194) on heating with piperidine but coumarin itself gave 2 -hydroxycinnamic acid amides. The behaviour of coumarin-3-carboxylic acid with amines depends on the ratio of reactants and the temperature. When 8-acetyl-7-hy(iroxy-4-methylcoumarin was subjected to a Mannich reaction, the benzodipyran (195) was formed in 80% yield.Several other tricyclic products have been prepared from coumarins for example, the... 

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