反応 #44868

反応方程式

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

HCl

→

title compound

収率 87.3%

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

収率 87.3%

溶媒

acetic acid

反応条件

後処理

1. 1
   温度at reflux for 18 h
2. 2
   温度After cooling
3. 3
   濃縮the reaction mixture was concentrated
4. 4
   抽出extracted with CH2Cl2 (150 mL) for three times
5. 5
   乾燥The combined extracts were dried over Na2SO4
6. 6
   ろ過filtered
7. 7
   濃縮concentrated
8. 8
   その他The residue was chromatographed on a column of silica gel
9. 9
   洗浄eluted with MeOH/CH2Cl2 (1:10)

実験手順

A mixture of Methyl 1-{[4-({[(3-isopropyl-2-oxo-2,3-dihydro-1H-benzimidazol-1-yl)carbonyl]amino}methyl)piperidin-1-yl]methyl}cyclopentanecarboxylate (1.33 g, 2.90 mmol, Step 4) in 4N-HCl (6 mL) and acetic acid (6 mL) was stirred at reflux for 18 h . After cooling, the reaction mixture was concentrated and basified with sat. NaHCO3 aq. (100 mL), extracted with CH2Cl2 (150 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 (1:10) to give 1.12 g (85%) of title compound as white solid. The crude compound was recrystallized from EtOAc×2 and dried in vacuo at 50° C. for 2 days to give 610 mg of title compound as white crystal.

出典