Reacción #45072

Ecuación de reacción

(trimethylsilyl)diazomethane

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

(trimethylsilyl)diazomethane

→

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

Rendimiento 44.2%

Disolventes

DCM

DCM

toluene

methanol

Condiciones de reacción

Tratamiento posterior

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

Procedimiento

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.

Fuente