تفاعل #47026

معادلة التفاعل

intermediate 76

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

4-fluorobenzylamine

→

product 193

المردود 98.1%

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

المردود 98.1%

المذيبات

dichloromethane

ظروف التفاعل

المعالجة

1. 1
   أخرى(reaction block) overnight
2. 2
   درجة الحرارةThe reaction mixture is cooled to RT
3. 3
   غسيلwashed with 0.1N HCl, and brine
4. 4
   أخرىThe solvent is evaporated
5. 5
   أخرىthe residue triturated with EtOAc
6. 6
   ترشيحthe insoluble material filtered

الإجراء التجريبي

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)

المصدر