반응 #42597

반응 방정식

dimethyl 5-bromoisophthalate

N-benzylpiperazine

cesium carbonate

BINAP

→

dimethyl 5-(4-benzylpiperazin-1-yl)isophthalate

수율 65.3%

용매

toluene

반응 조건

후처리

1. 1
   기타to yield a yellow solution with a white suspension
2. 2
   온도The reaction mixture was cooled to room temperature
3. 3
   여과vacuum filtered
4. 4
   세척the solid rinsed with fresh toluene
5. 5
   농축The filtrate was then concentrated under reduced pressure
6. 6
   기타to yield a yellow oil
7. 7
   기타Purification by flash chromatography (silica, 80:20 hexanes/ethyl acetate)

실험 절차

In a sealed tube, a solution of dimethyl 5-bromoisophthalate (5.0 g, 18.3 mmol), N-benzylpiperazine (4.0 mL, 23.0 mmol), and cesium carbonate (8.4 g, 25.7 mmol) in toluene (36 mL) was degassed with nitrogen at room temperature for 20 minutes. Palladium (II) acetate (225 mg, 0.92 mmol) and BINAP (1.7 g, 2.74 mmol) were quickly added under nitrogen and the solution heated to 80° C. overnight to yield a yellow solution with a white suspension. The reaction mixture was cooled to room temperature, vacuum filtered, and the solid rinsed with fresh toluene. The filtrate was then concentrated under reduced pressure to yield a yellow oil. Purification by flash chromatography (silica, 80:20 hexanes/ethyl acetate) gave the desired dimethyl 5-(4-benzylpiperazin-1-yl)isophthalate (4.40 g): ESI MS m/z 369 [M+H]+.

출처