Reaktion #410393

Reaktionsgleichung

1-(3,4,5-trimethoxybenzoyl)-3-phenyl-3-(2-methanesulfonyloxyethyl)pyrrolidine

ethyl acetate

N,N-diisopropylethylamine

ethyl acetate

(1(4-fluorobenzyl)-1H-benzimidazol-2-yl)(piperidin-4-yl)amine

→

title compound

1-(3,4,5-trimethoxybenzoyl)-3-(2-(4-(1-(4-fluorobenzyl)-1H-benzimidazol-2-yl-amino)piperidin-1-yl)ethyl)-3-phenylpyrrolidine

Lösungsmittel

acetonitrile

methanol ethyl acetate

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturHeat to reflux
2. 2
   ExtraktionExtract twice with water, saturated aqueous sodium bicarbonate solution, and aqueous sodium chloride solution
3. 3
   TrocknenDry the organic layer over Na2SO4
4. 4
   Filtrationfilter
5. 5
   Einengenconcentrate in vacuo
6. 6
   Sonstigeto obtain a residue
7. 7
   SonstigeEvaporate the product
8. 8
   workup.ADDITIONcontaining fractions
9. 9
   Sonstigepartition between dichloromethane and 1/1 brine/water
10. 10
    TrocknenDry the organic layer over Na2SO4
11. 11
    Filtrationfilter
12. 12
    Einengenconcentrate in vacuo

Vorschrift

Combine 1-(3,4,5-trimethoxybenzoyl)-3-phenyl-3-(2-methanesulfonyloxyethyl)pyrrolidine (0.42 g, 0.9 mmol) and (1(4-fluorobenzyl)-1H-benzimidazol-2-yl)(piperidin-4-yl)amine (0.49 g, 1.5 mmol), and N,N-diisopropylethylamine (0.40 mL, 2.3 mmol) in acetonitrile (12 mL). Heat to reflux. After 18 hours, pour the reaction mixture into ethyl acetate. Extract twice with water, saturated aqueous sodium bicarbonate solution, and aqueous sodium chloride solution. Dry the organic layer over Na2SO4, filter, and concentrate in vacuo to obtain a residue. Chromatograph the residue on a short column of silica gel eluting sequentially with ethyl acetate and then 25% methanol/ethyl acetate. Evaporate the product containing fractions and partition between dichloromethane and 1/1 brine/water. Dry the organic layer over Na2SO4, filter, and concentrate in vacuo to give the title compound: Rf=0.38 silica gel, 25% methanol/ethyl acetate).

Quelle