31468-18-5

Usage

InChI:InChI=1/C8H16N2O/c1-9(2)8(11)10-6-4-3-5-7-10/h3-7H2,1-2H3

Upstream product

• 110-89-4 piperidine 
• 79-44-7 N,N-Dimethylcarbamoyl chloride 
• 110-86-1 pyridine 

Downstream Products

• 2851-12-9 2-(piperidin-1-yl)-1H-benzo[d]imidazole 
• 2851-09-4 2-(piperidin-1-yl)-1,3-benzoxazole 

Relevant academic research and scientific papers

Synthetic and structural studies of piperidine carboxamide uranyl ion complexes

New piperidine based ligands of the type [C5H 10NCONR2] (where R = CH3 (L1), C 2H5 (L2) and iC3H7 (L3)) have been prepared and characterized. The complex ch

Chloroformamidinium salts: Efficient reagents for preparation of 2-aminobenzoimidazole, 2-aminobenzoxazole, and 2-aminobenzothiazole derivatives

A Reaction involving chloroformamidinium salts (TCFH 1a, BTCFH 1b, DmCFH 1c, DmPCFH 1d, BPCFH 1e) and 2-aminophenol 9a, benzene-1,2-diamine 9b, and 2-aminothiophenol 9c afforded 2-aminobenzoxazole 13, 2-aminobenzoimidazole 14, and 2-aminobenzothiazole 15 derivatives, respectively as major products, due to the in situ heterocyclization with dimethylamine acting as the better leaving group. Attempts for preparation of 13-15 from the reaction of N,N-dimethyl carbomyl chloride 16 with 2-aminophenol 9a, benzene-1,2-diamine 9b, and 2-aminothiophenol 9c were unsuccessful, and gave the unexpected products benzoxazol-2-ol 18a, benzoimidazol-2-one 18b, and S-(2-amino-phenyl) N,N-dimethylthiocarbamate 19 respectively. On the other hand reaction of chloroformamidinium salts 1a-e with 3-benzyl-2-hydrazinoquinoxaline 3 and 1-hydrazinophthalazine hydrochloride 4 in the presence of triethylamine as a base, afforded the [1,2,4]triazolo derivatives 6 and 7 respectively in good yield and purity. These triazole derivatives were formed due to the strong tendency towards heterocyclization and substitution of dimethylamine group as a better leaving group.

Design and synthesis of new immonium-type coupling reagents

A new family of immonium-type coupling reagents is de-scribed here. The differences in the carbocation skeletons of these reagents can be correlated with differences in stability and thus reactivity. The dihydroimidazole derivatives are highly unstable to air, whereas the salts derived from dimethylamine are the most stable and the pyrrolidino derivatives are of intermediate stability. These results should be taken into account mainly when coupling reagents are deposited in open vessels, such in some automatic synthesizers. As regards both coupling yield and retention of configuration, HOAt derivatives have been confirmed to be superior to those of HOBt in all cases. For peptides containing hindered residues, fluoroformamidinium salts are more convenient than the HOAt-based reagents. Wiley-VCH Verlag GmbH & Co. KGaA, 2006.