反応 #1014059

反応方程式

potassium iodide

N1,N1-diethyl-N2-methylethane-1,2-diamine

4-(chloromethyl)benzoic acid

potassium carbonate

→

4-(((2-(diethylamino)ethyl)(methyl)amino)methyl)benzoic acid

溶媒

N,N-dimethylformamide

反応条件

後処理

1. 1
   その他Into a 1000-mL round bottom flask, was placed
2. 2
   ろ過The solids were filtered out
3. 3
   濃縮The resulting mixture was concentrated under vacuum
4. 4
   その他The crude product (10 g) was purified by reverse phase chromatography
5. 5
   洗浄eluting with a water/methanol gradient
6. 6
   その他This resulted in 5 g (27%) of 4-(((2-(diethylamino)ethyl)(methyl)amino)methyl)benzoic acid as a white solid

実験手順

Into a 1000-mL round bottom flask, was placed a solution of N1,N1-diethyl-N2-methylethane-1,2-diamine (10 g, 69.23 mmol, 1.20 equiv, 90%) in N,N-dimethylformamide (500 mL), 4-(chloromethyl)benzoic acid (11.5 g, 67.65 mmol, 1.00 equiv), potassium carbonate (10 g, 71.94 mmol, 3.00 equiv), and potassium iodide (1.95 g, 11.75 mmol, 0.20 equiv). The resulting solution was stirred for 2 h at 90° C. in an oil bath. The solids were filtered out. The resulting mixture was concentrated under vacuum. The crude product (10 g) was purified by reverse phase chromatography eluting with a water/methanol gradient. This resulted in 5 g (27%) of 4-(((2-(diethylamino)ethyl)(methyl)amino)methyl)benzoic acid as a white solid. 1H-NMR (300 MHz, CDCl3, ppm): δ 8.00(d, J=8.4 Hz, 2H), 7.39(d, J=8.1 Hz, 2H), 3.68(s, 2H), 3.23-3.15(m, 6H), 2.91(m, 2H), 2.33(s, 3H), 1.33-1.27(m, 6H). MS (ES, m/z): 265 [M+H]+.

出典