反応 #73018

反応方程式

triethylamine

Triethylamine

4-chloro-3-nitro-1,5-naphthyridine

1-aminomethyl-1-cyclohexanol hydrochloride

→

1-{[(3-nitro[1,5]naphthyridin-4-yl)amino]methyl}cyclohexanol

収率 100.0%

溶媒

dichloromethane

反応条件

後処理

1. 1
   workup.WAITAfter 30 min
2. 2
   その他the solution was partitioned between saturated aqueous sodium bicarbonate (100 mL) and chloroform (200 mL)
3. 3
   抽出The aqueous layer was extracted with chloroform (3×200 mL)
4. 4
   洗浄The combined organic extracts were washed with saturated aqueous sodium bicarbonate (2×100 mL) and brine (80 mL)
5. 5
   乾燥dried over MgSO4
6. 6
   ろ過filtered
7. 7
   濃縮concentrated under reduced pressure
8. 8
   その他dried under vacuum

実験手順

Triethylamine (8.38 mL, 60.1 mmol) was added over 10 min to a stirred mixture of 4-chloro-3-nitro-1,5-naphthyridine (6.00 g, 28.6 mmol) and 1-aminomethyl-1-cyclohexanol hydrochloride (5.00 g, 30.1 mmol) in dichloromethane (115 mL) at 0° C. The solution was allowed to warm to rt and more 1-aminomethyl-1-cyclohexanol hydrochloride (0.2 g) was added. The solution was stirred overnight and more triethylamine (0.5 mL) was added. After 30 min, the solution was partitioned between saturated aqueous sodium bicarbonate (100 mL) and chloroform (200 mL). The aqueous layer was extracted with chloroform (3×200 mL). The combined organic extracts were washed with saturated aqueous sodium bicarbonate (2×100 mL) and brine (80 mL), dried over MgSO4, filtered, concentrated under reduced pressure, and dried under vacuum to afford 1-{[(3-nitro[1,5]naphthyridin-4-yl)amino]methyl}cyclohexanol as a yellow solid (8.65 g, 100%).

出典