反应 #806310

反应方程式

1-(4-chloro-phenyl)-3-cyclopentyl-propane-1,2-diamine

ethyl 2-ethoxy-4-methoxy-benzimidate hydrochloride

triethylamine

→

5-(4-chloro-phenyl)-4-cyclopentylmethyl-2-(2-ethoxy-4-methoxy-phenyl)-4,5-dihydro-1H-imidazole

收率 63.0%

溶剂

ethanol

反应条件

后处理

1. 1
   温度The reaction mixture was heated
2. 2
   温度at gentle reflux for 6 h
3. 3
   其他The solvent was removed
4. 4
   其他the residue was partitioned between water and methylene chloride
5. 5
   萃取The product was extracted with methylene chloride (2×20 mL)
6. 6
   洗涤The organic layers were washed with brine
7. 7
   干燥dried over anhydrous sodium sulfate
8. 8
   浓缩concentrated in vacuo
9. 9
   其他The residue was purified by flash chromatography (Biotage system, KP-Sil™ 32–63 μm, 60 Å silica gel)
10. 10
    洗涤eluting with ethyl acetate

实验过程

To a solution of 1-(4-chloro-phenyl)-3-cyclopentyl-propane-1,2-diamine (170 mg, 0.672 mmol) and ethyl 2-ethoxy-4-methoxy-benzimidate hydrochloride (210 mg, 0.806 mmol) in ethanol (10 mL) was added triethylamine (82 μL, 0.806 mmol). The reaction mixture was heated at gentle reflux for 6 h. The solvent was removed and the residue was partitioned between water and methylene chloride. The product was extracted with methylene chloride (2×20 mL). The organic layers were washed with brine, dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was purified by flash chromatography (Biotage system, KP-Sil™ 32–63 μm, 60 Å silica gel) eluting with ethyl acetate then 5–10% methanol in ethyl acetate to give 5-(4-chloro-phenyl)-4-cyclopentylmethyl-2-(2-ethoxy-4-methoxy-phenyl)-4,5-dihydro-1H-imidazole (174 mg, 63%, 4.5:1.0 ratio of cis:trans) as a white foam. HR-MS (ES, m/z) observed 413.1993, calculated for C24H30N2O2Cl [(M+H)+] 413.1991.

来源