Реакция #44762

Уравнение реакции

sodium bicarbonate

triethylamine

methyl 4-(bromomethyl)benzoate

N,N′-dimethylethan-1,2-diamine

→

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

Выход 62.0%

Растворители

tetrahydrofuran

Условия реакции

Обработка

1. 1
   Температураto reflux for two hours
2. 2
   ТемператураAfter cooling
3. 3
   ЭкстракцияThe mixture was extracted with ethyl acetate
4. 4
   ПромывкаThe organic layer was washed with brine
5. 5
   Сушкаdried over sodium sulfate
6. 6
   Концентрированиеconcentrated under reduced pressure

Методика

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.

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