ChemicalBook CAS DataBase List 1-BENZYL-1,4-DIHYDRONICOTINAMIDE

1-BENZYL-1,4-DIHYDRONICOTINAMIDE synthesis

12synthesis methods

Product Name:1-BENZYL-1,4-DIHYDRONICOTINAMIDE
CAS Number:952-92-1
Molecular formula:C13H14N2O
Molecular Weight:214.26

Ethanamine, N-[(3,5-dichlorophenyl)methylene]-2,2-diethoxy-

1000210-73-0
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952-92-1
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Yield: 73%

Reaction Conditions:

with sodium dithionite;sodium carbonate in water at 20; for 0.25 h;Darkness;Inert atmosphere;

Steps:

5.2 synthesis of 1-benzyl-1,4-dihydropyridine-3-carboxamide
To a solution of 1 -benzylpyridinium-3 carboxamide iodide (1 g, 3.41 mmol) in H20 (15 mL) was added sodium carbonate (1.44 g, 13.64 mmol) and sodium dithionite (2.65 g, 12.96 mmol) at room temperature. The resulting solution was stirred under nitrogen in darkness for 15 mn. The reaction mixture was then extracted with dichioromethane. The combined organic phases were dried overNaSO, filtered and evaporated under reduced pressure at room temperature to afford N-benzyl4 ,4- dihydronicotinamide (BNAH) (0.530 g, 73%).1HNMR(CDCl3, 300 MHz, 298K, 8 ppm): 7.34 (m, 5 H), 7.26 (s, I H), 5.75 (d, 1 H,J= 8,10Hz),5.38 (s, 2 H), 4.76 (m, 1 H), 4.30 (s, 2 H), 3.19 (s, 2 H).13C NMR (CDC13, 75.5 MHz, 298 K, 8 ppm): 140.15, 137.37, 129.09, 128.95, 127.92, 127.29,103.34, 98.75, 57.52, 22.97.

References:

INSA (INSTITUT NATIONAL DES SCIENCES APPLIQUéES) DE ROUEN;CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE (CNRS);UNIVERSITE DE ROUEN;VFP THéRAPIES;MARSAIS, Francis;LEVACHER, Vincent;PAPAMICAEL, Cyril;BOHN, Pierre;PEAUGER, Ludovic;GEMBUS, Vincent;LE FUR, Nicolas;DUMARTIN-LEPINE, Marie-Laurence WO2014/114742, 2014, A1 Location in patent:Page/Page column 37; 38

13076-43-2 Synthesis