Reaktion #1014059

Reaktionsgleichung

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

Lösungsmittel

N,N-dimethylformamide

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeInto a 1000-mL round bottom flask, was placed
2. 2
   FiltrationThe solids were filtered out
3. 3
   EinengenThe resulting mixture was concentrated under vacuum
4. 4
   SonstigeThe crude product (10 g) was purified by reverse phase chromatography
5. 5
   Wascheneluting with a water/methanol gradient
6. 6
   SonstigeThis resulted in 5 g (27%) of 4-(((2-(diethylamino)ethyl)(methyl)amino)methyl)benzoic acid as a white solid

Vorschrift

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]+.

Quelle