Reaktion #44762

Reaktionsgleichung

sodium bicarbonate

triethylamine

methyl 4-(bromomethyl)benzoate

N,N′-dimethylethan-1,2-diamine

→

methyl 4-[(methyl(2-(methylamino)ethyl)amino)methyl]benzoate

Ausbeute 62.0%

Lösungsmittel

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturto reflux for two hours
2. 2
   TemperaturAfter cooling
3. 3
   ExtraktionThe mixture was extracted with ethyl acetate
4. 4
   WaschenThe organic layer was washed with brine
5. 5
   Trocknendried over sodium sulfate
6. 6
   Einengenconcentrated under reduced pressure

Vorschrift

A mixture of methyl 4-(bromomethyl)benzoate (2 g, 8.73 mmol) and N,N′-dimethylethan-1,2-diamine (7.5 mL, 70 mmol) was heated with triethylamine (9.8 mL, 70 mmol) in tetrahydrofuran (80 mL) to reflux for two hours. After cooling, the mixture was treated with saturated sodium bicarbonate solution. The mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate, and concentrated under reduced pressure. Flash chromatography gave 1.28 g of methyl 4-[(methyl(2-(methylamino)ethyl)amino)methyl]benzoate, 1H NMR (300 MHz, CD3OD) δ 7.97 (d, 2H), 7.45 (d, 2H), 3.59 (s, 2H), 2.67 (m, 2H), 2.54 (m, 2H), 2.35 (s, 3H), 2.22 (s, 3H) ppm.

Quelle