Реакция #45072

Уравнение реакции

(trimethylsilyl)diazomethane

4-((4-methylpiperazin-1-yl)methyl)benzoic acid

(trimethylsilyl)diazomethane

→

methyl 4-((4-methylpiperazin-1-yl)methyl)benzoate

Выход 44.2%

Растворители

DCM

DCM

toluene

methanol

Условия реакции

Обработка

1. 1
   workup.STIRRINGthe solution was stirred at room temperature for a further 18 h
2. 2
   ДругоеThe reaction mixture was evaporated to dryness
3. 3
   Другоеto afford the crude product (0.723 g) as a white solid
4. 4
   Фильтрацияthe insolubles were filtered off
5. 5
   ДругоеThe filtrate was evaporated to dryness
6. 6
   Другоеto afford the crude product
7. 7
   Фильтрацияmore insolubles were filtered off

Методика

A solution of (trimethylsilyl)diazomethane ((0.611 mL, 3.84 mmol) 2.0M in diethyl ether) was added dropwise to a stirred suspension of 4-((4-methylpiperazin-1-yl)methyl)benzoic acid (0.75 g, 3.20 mmol) in toluene (21 mL) and methanol (7 mL) over a period of 10 mins under nitrogen. The resulting suspension was stirred at room temperature for 3 h. A further aliquot of (trimethylsilyl)diazomethane (1.222 mL, 7.68 mmol) was added dropwise and the solution was stirred at room temperature for a further 18 h. The reaction mixture was evaporated to dryness to afford the crude product (0.723 g) as a white solid. This was taken up in DCM and the insolubles were filtered off. The filtrate was evaporated to dryness to afford the crude product. This was taken up in DCM again and more insolubles were filtered off to afford methyl 4-((4-methylpiperazin-1-yl)methyl)benzoate (0.351 g, 44.2%), which was used without purification.

Источник