596129-27-0

Usage

Derived from

piperidine (a cyclic secondary amine)

Esterification

with 2-tert-butoxycarbonylamino-phenylacetyl chloride

Pharmacological and biological activities

known for its potential applications in medicine and research

Use as a building block

for the synthesis of various pharmaceuticals and biologically active compounds due to its unique structural characteristics

Chirality

(2S)indicates the compound has a specific three-dimensional arrangement of atoms, which can affect its biological activity and properties.

Upstream product

• 26250-84-0 (S)-(-)-1-(tert-butoxycarbonyl)-2-piperidinecarboxylic acid 
• 100-46-9 benzylamine 
• 24424-99-5 di-tert-butyl dicarbonate 
• 596129-26-9 (S)-1-(2,2,2-Trifluoro-acetyl)-piperidine-2-carboxylic acid (S)-3,4,4-trimethyl-2-oxo-tetrahydro-furan-3-yl ester 
• 596129-25-8 (+/-)-N-trifluoroacetyl pipecolic acid 
• 58632-95-4 2-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrile 
• 3105-95-1 pipecolinic acid 

Downstream Products

• 1178548-92-9 C₁₄H₁₈N₂O₂ 

Relevant academic research and scientific papers

New chiral lewis bases derived from l-pipecolinic acid showing stereocontrol highly dependent on the catalyst design in the hydrosilylation of N-phenyl ketimines

Chiral L-pipecolinic acid based catalysts, the N-functionalized pipecolinamides 4a-h and 5a-e, have been obtained in a straightforward two-step synthesis starting from BOC-Lpipecolinic acid. The catalysts form, a complex with trichlorosilane, which proved

Diastereoselective esterification of (±)-N-trifluoroacetyl pipecolic acid using (S)-α-methyl pantolactone: Synthesis of (S)-N-Boc pipecolic acid and (S)-N-Boc-2-piperidinemethanol

Racemic N-trifluoroacetyl pipecolic acid has been converted into (S)-N-Boc-pipecolic acid or (S)-N-Boc-2-piperidinemethanol by DCC/DMAP-induced diastereoselective esterification with (S)-α-methyl pantolactone, followed by a saponification or a reduction reaction and N-Boc protection.

Synthesis of 2-piperidinecarboxylic acid derivatives as potential anticonvulsants

A variety of 2-piperidinecarboxamides were synthesized and evaluated for anticonvulsant activity using the MES and sc PTZ tests in mice and rats. Neurotoxicity was determined by the rotorod test. Several N-(benzyl)-2- piperidinecarboxamides exhibited potent MES activity in mice [2-CF3 14, ED50 = 29 mg/kg; 3-F 16, ED50 = 31 mg/kg; and 3-CF3 17, ED50 = 24 mg/kg]. The most active compounds in the MES test in mice were the 2,6- dimethylanilides [(R,S)-34, ED50 = 5.8 mg/kg; (R)-35, ED50 = 5.7 mg/kg; and (S)-36, ED50 = 14.8 mg/kg]. The enantiomer (S)-36 was about two-fold less potent in the MES test than (R)-35 and also was less neurotoxic. Acylation of the piperidine ring nitrogen of 12 anal 34 led to a decrease in the MES activity. In the N-(α-methylbenzyl)-2-piperidine-carboxamides, the stereochemistry at either the 2-position of the piperidine ring or at the α- position of the N-(α-methylbenzyl) group does not significantly affect MES activity.