Reacción #66249

Ecuación de reacción

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

Disolventes

DCM

DCM

Condiciones de reacción

Tratamiento posterior

1. 1
   Lavadoto wash the solution
2. 2
   OtroOrganic layer was separated
3. 3
   Extracciónthe aqueous layer was extracted with DCM
4. 4
   LavadoThe combined organic layers were washed by water
5. 5
   Secadodried over MgSO4
6. 6
   OtroEvaporation of solvent
7. 7
   Otrogave a crude product, which
8. 8
   Otrowas purified by chromatography on silica gel eluting with MeOH-DCM

Procedimiento

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+).

Fuente