تفاعل #44874

معادلة التفاعل

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

المردود 16.0%

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

المردود 16.0%

المذيبات

NaHCO3

THF

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةwas refluxed for 18 h
2. 2
   درجة الحرارةAfter cooling
3. 3
   استخلاصextracted with CH2Cl2 (100 mL) for three times
4. 4
   تجفيفThe combined extracts were dried over Na2SO4
5. 5
   ترشيحfiltered
6. 6
   تركيزconcentrated
7. 7
   أخرىThe residue was chromatographed on a column of silica gel
8. 8
   غسيلeluted with MeOH/CH2Cl2 (1:20→1:10)
9. 9
   غسيلNH-silica gel eluted with EtOAc/hexane (1:5→1:2)

الإجراء التجريبي

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.

المصدر