Réaction #47019

Équation de réaction

(cis-4,5-diphenyl-4,5-dihydro-1H-imidazol-2-yl)-(4-fluorobenzyl)amine

(cis-4,5-Diphenyl-4,5-dihydro-1H-imidazol-2-yl)-(4-fluorobenzyl)amine hydrochloride

triethylamine

phenyl chloroformate

→

product 123

Rendement 82.6%

2-(4-Fluorobenzylamino)-cis-4,5-diphenyl-4,5-dihydro-imidazole-1-carboxylic acid phenyl ester

Rendement 82.6%

Solvants

dichloromethane

dichloromethane

Conditions de réaction

Traitement

1. 1
   Lavagewashed with water
2. 2
   Séchagethe organic layer is dried (MgSO4)
3. 3
   Filtrationfiltered
4. 4
   Autreevaporated
5. 5
   AutreThe residue is purified by chromatography on silica gel
6. 6
   Lavagegradient elution with heptane:EtOAc (70:30-60:40)

Mode opératoire

To a solution of (cis-4,5-diphenyl-4,5-dihydro-1H-imidazol-2-yl)-(4-fluorobenzyl)amine (86) (100 mg, 0.26 mmol), triethylamine (0.091 mL, 0.656 mmol), 4-dimethylamino-pyridine (10 mg) in dichloromethane (10 mL) is added phenyl chloroformate (0.033 mL, 0.262 mmol), and the mixture is stirred at RT overnight. The reaction mixture is diluted with dichloromethane and washed with water, and the organic layer is dried (MgSO4), filtered, and evaporated. The residue is purified by chromatography on silica gel; gradient elution with heptane:EtOAc (70:30-60:40) gives 100 mg of the product 123. 1H NMR (CDCl3) δ 7.50-7.40 (m, 2 H), 7.40-7.10 (m, 6 H), 7.10-6.90 (m, 8 H), 6.90-6.80 (m, 2 H), 6.70-6.60 (m, 2 H), 5.75-5.55 (m, 2 H), 4.75-4.55 (m, 2 H); MS: m/z 466 (M++1)

Source