Réaction #47026

Équation de réaction

intermediate 76

cis-3a,4,5,6,7,7a-Hexahydro-2-methylthio-benzimidazole-1-carboxylic acid, tert-butyl ester

4-fluorobenzylamine

→

product 193

Rendement 98.1%

2-[(4-Fluorobenzyl)amino]-cis-3a,4,5,6,7,7a-hexahydro-1H-benzimidazol-1-carboxylic acid tert-butyl ester

Rendement 98.1%

Solvants

dichloromethane

Conditions de réaction

Traitement

1. 1
   Autre(reaction block) overnight
2. 2
   TempératureThe reaction mixture is cooled to RT
3. 3
   Lavagewashed with 0.1N HCl, and brine
4. 4
   AutreThe solvent is evaporated
5. 5
   Autrethe residue triturated with EtOAc
6. 6
   Filtrationthe insoluble material filtered

Mode opératoire

A mixture of intermediate 76 (200 mg, 0.0.740 mmol), 4-fluorobenzylamine (0.5 mL, 4.4 mmol) is heated at 100° C. (reaction block) overnight. The reaction mixture is cooled to RT. The reaction mixture is diluted with dichloromethane, washed with 0.1N HCl, and brine. The solvent is evaporated, and the residue triturated with EtOAc, and the insoluble material filtered to give 252 mg of the product 193. 1H NMR (CDCl3) δ 8.55 (s, 1 H), 7.55-7.35 (m, 2 H), 7.10-7.00 (m, 2 H), 5.10-4.90 (m, 2 H), 4.30-4.10 (m, 2 H), 2.70-2.55 (m, 1 H), 2.20-2.05 (m, 1 H), 1.80-1.05 (m, 15 H); MS: m/z 348 (M++1)

Source