Реакция #45055

Уравнение реакции

1-isopropylpiperazine

methyl 4-bromobenzoate

potassium carbonate

→

methyl 4-(4-propan-2-yl-piperizin-1-yl)benzoate

Выход 64.8%

Растворители

DME

Условия реакции

Обработка

1. 1
   Другоеsealed into a microwave tube
2. 2
   Температураcooled to room temperature
3. 3
   ДругоеThe reaction mixture was evaporated to dryness
4. 4
   workup.DISSOLUTIONredissolved in EtOAc (25 mL)
5. 5
   Промывкаwashed sequentially with water (15 mL) and saturated brine (15 mL)
6. 6
   СушкаThe organic layer was dried over MgSO4
7. 7
   Фильтрацияfiltered
8. 8
   Другоеevaporated
9. 9
   Другоеto afford crude product
10. 10
    ДругоеThe crude product was purified by silica column chromatography
11. 11
    Промывкаeluting with 5% MeOH in DCM
12. 12
    ДругоеPure fractions were evaporated to dryness

Методика

Tris(dibenzylideneacetone)dipalladium(0) (0.014 g, 0.02 mmol) was added to a deoxygenated suspension of 1-isopropylpiperazine (0.151 g, 1.18 mmol), methyl 4-bromobenzoate (0.215 g, 1 mmol), potassium carbonate (0.193 g, 1.4 mmol) and 2-dicyclohexylphosphino-2′-(N,N-dimethylamino)biphenyl (0.012 g, 0.03 mmol) in DME (4 mL), and sealed into a microwave tube. The reaction was heated to 130° C. for 10 mins in the microwave reactor and cooled to room temperature. The reaction mixture was evaporated to dryness, redissolved in EtOAc (25 mL) and washed sequentially with water (15 mL) and saturated brine (15 mL). The organic layer was dried over MgSO4, filtered and evaporated to afford crude product. The crude product was purified by silica column chromatography, eluting with 5% MeOH in DCM. Pure fractions were evaporated to dryness to afford methyl 4-(4-propan-2-yl-piperizin-1-yl)benzoate (0.170 g, 64.8%) as a tan solid.

Источник