Reaktion #45072

Reaktionsgleichung

(trimethylsilyl)diazomethane

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

(trimethylsilyl)diazomethane

→

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

Ausbeute 44.2%

Lösungsmittel

DCM

DCM

toluene

methanol

Reaktionsbedingungen

Aufarbeitung

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

Vorschrift

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.

Quelle