Reacción #44874

Ecuación de reacción

3-isopropyl-2-oxo-N-(piperidin-4-ylmethyl)-2,3-dihydro-1H-benzimidazole-1-carboxamide

3-Isopropyl-2-oxo-N-(piperidin-4-ylmethyl)-2,3-dihydro-1H -benzimidazole-1-carboxamide

tert-butyl acrylate

→

title compound

Rendimiento 16.0%

tert-butyl 3-[4-({[(3-isopropyl-2-oxo-2,3-dihydro-1H -benzimidazol-1-yl)carbonyl]amino}methyl)piperidin-1-yl]propanoate

Rendimiento 16.0%

Disolventes

NaHCO3

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturawas refluxed for 18 h
2. 2
   TemperaturaAfter cooling
3. 3
   Extracciónextracted with CH2Cl2 (100 mL) for three times
4. 4
   SecadoThe combined extracts were dried over Na2SO4
5. 5
   Filtraciónfiltered
6. 6
   Concentraciónconcentrated
7. 7
   OtroThe residue was chromatographed on a column of silica gel
8. 8
   Lavadoeluted with MeOH/CH2Cl2 (1:20→1:10)
9. 9
   LavadoNH-silica gel eluted with EtOAc/hexane (1:5→1:2)

Procedimiento

A mixture of 3-isopropyl-2-oxo-N-(piperidin-4-ylmethyl)-2,3-dihydro-1H-benzimidazole-1-carboxamide (0.50 g, 1.58 mmol, Step 2), tert-butyl acrylate (0.340 mL, 2.37 mmol) and iPrNEt (0.275 mL, 2.37 mmol) in THF (20 mL) was refluxed for 18 h. After cooling, the reaction mixture was diluted with sat. NaHCO3 aq. (100 mL), extracted with CH2Cl2 (100 mL) for three times. The combined extracts were dried over Na2SO4, filtered and concentrated. The residue was chromatographed on a column of silica gel eluted with MeOH/CH2Cl2 (1:20→1:10) and then NH-silica gel eluted with EtOAc/hexane (1:5→1:2) to give 0.111 g (16%) of title compound as colorless syrup.

Fuente