Benzyl N-[4-(cyanomethyl)phenyl]carbamate synthesis

Yield:861250-54-6 95%

Reaction Conditions:

in 1,4-dioxane at 20; for 1 h;

Steps:

62.2 Stage 62.2 [4-(Cyano-methyl)-phenyl]-carbamic acid benzyl ester

(4-Amino-phenyl)-acetonitrile (2 g, 15.1 mmol) and dibenzyl dicarbonate (4.33 g, 15.1 mmol) dissolved in dioxane (16 mL) are stirred for 1 hour at RT. After evaporating the solvent, the product is isolated by flash chromatography (silica gel, 4.5×25 cm, CH₂Cl₂/MeOH=99:1): white solid (3.82 g, 14.4 mmol; 95%); ES-MS: M-H=265.0; R_f(CH₂Cl₂/MeOH=95:5)=0.49; HPLC: ^At_Ret=6.32 minutes. ¹H-NMR (400 MHz, DMSO-d₆): 9.82 (s, 1H, NH), 7.51-7.35 (m, 7H, aryl), 7.26 (d, 8.5 Hz, 2H, aryl), 5.15 (s, 2H, CH₂), 3.95 (s, 2H, CH₂).

References:

US2005/222171,2005,A1 Location in patent:Page/Page column 41