反応 #42597

反応方程式

dimethyl 5-bromoisophthalate

N-benzylpiperazine

cesium carbonate

BINAP

→

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

収率 65.3%

溶媒

toluene

反応条件

後処理

1. 1
   その他to yield a yellow solution with a white suspension
2. 2
   温度The reaction mixture was cooled to room temperature
3. 3
   ろ過vacuum filtered
4. 4
   洗浄the solid rinsed with fresh toluene
5. 5
   濃縮The filtrate was then concentrated under reduced pressure
6. 6
   その他to yield a yellow oil
7. 7
   その他Purification by flash chromatography (silica, 80:20 hexanes/ethyl acetate)

実験手順

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]+.

出典