Реакция #66249

Уравнение реакции

N-methyl 3-(4-fluorobenzoyl)-1,2,3,4,5,6-hexahydroazepino[4,5-b]indole-5-carbamide

tert-butyl hypochloride

water

→

title compound

N-Methyl 3-(4-Fluorobenzoyl)-1,2,3,6-Tetrahydroazepino[4,5-b]Indole-5-Carbamide

Растворители

DCM

DCM

Условия реакции

Обработка

1. 1
   Промывкаto wash the solution
2. 2
   ДругоеOrganic layer was separated
3. 3
   Экстракцияthe aqueous layer was extracted with DCM
4. 4
   ПромывкаThe combined organic layers were washed by water
5. 5
   Сушкаdried over MgSO4
6. 6
   ДругоеEvaporation of solvent
7. 7
   Другоеgave a crude product, which
8. 8
   Другоеwas purified by chromatography on silica gel eluting with MeOH-DCM

Методика

To a solution of N-methyl 3-(4-fluorobenzoyl)-1,2,3,4,5,6-hexahydroazepino[4,5-b]indole-5-carbamide and TEA in DCM at 0° C. was added a cooled (0° C.) solution of tert-butyl hypochloride (57 mL, 0.5 mmol) in DCM. The reaction mixture was stirred for 1.5 hours at 0° C. Cold water was added to wash the solution. Organic layer was separated and the aqueous layer was extracted with DCM. The combined organic layers were washed by water and dried over MgSO4. Evaporation of solvent gave a crude product, which was purified by chromatography on silica gel eluting with MeOH-DCM to give the title compound (14 mg); 1H-NMR (CDCl3): δ 10.04 (1H, br s), 7.57 (2H, m), 7.52 (1H, d), 7.37 (1H, d), 7.24 (1H, m), 7.12 (4H, m) 5.9 (1H, br s), 4.15 (2H, t), 3.27 (2H, t), 2.92 (3H, d); MS (ES): 378 (MH+).

Источник