Reaktion #45055

Reaktionsgleichung

1-isopropylpiperazine

methyl 4-bromobenzoate

potassium carbonate

→

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

Ausbeute 64.8%

Lösungsmittel

DME

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigesealed into a microwave tube
2. 2
   Temperaturcooled to room temperature
3. 3
   SonstigeThe reaction mixture was evaporated to dryness
4. 4
   workup.DISSOLUTIONredissolved in EtOAc (25 mL)
5. 5
   Waschenwashed sequentially with water (15 mL) and saturated brine (15 mL)
6. 6
   TrocknenThe organic layer was dried over MgSO4
7. 7
   Filtrationfiltered
8. 8
   Sonstigeevaporated
9. 9
   Sonstigeto afford crude product
10. 10
    SonstigeThe crude product was purified by silica column chromatography
11. 11
    Wascheneluting with 5% MeOH in DCM
12. 12
    SonstigePure fractions were evaporated to dryness

Vorschrift

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.

Quelle