تفاعل #42597

معادلة التفاعل

dimethyl 5-bromoisophthalate

N-benzylpiperazine

cesium carbonate

BINAP

→

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

المردود 65.3%

المذيبات

toluene

ظروف التفاعل

المعالجة

1. 1
   أخرىto yield a yellow solution with a white suspension
2. 2
   درجة الحرارةThe reaction mixture was cooled to room temperature
3. 3
   ترشيحvacuum filtered
4. 4
   غسيلthe solid rinsed with fresh toluene
5. 5
   تركيزThe filtrate was then concentrated under reduced pressure
6. 6
   أخرىto yield a yellow oil
7. 7
   أخرىPurification by flash chromatography (silica, 80:20 hexanes/ethyl acetate)

الإجراء التجريبي

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]+.

المصدر