Reaktion #410416

Reaktionsgleichung

2-chloroethyl ethyl ether

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

dimethylformamide

sodium hydride

→

methanol ethyl acetate triethylamine

Lösungsmittel

methanol ethyl acetate triethylamine

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.WAITAfter 18 hours
2. 2
   Temperaturcool to ambient temperature
3. 3
   ExtraktionExtract three times with water
4. 4
   Trocknendry the organic layer over Na2SO4
5. 5
   Filtrationfilter
6. 6
   Sonstigeevaporate in vacuo
7. 7
   Sonstigeto give a residue
8. 8
   SonstigeCollect the product
9. 9
   workup.ADDITIONcontaining fractions
10. 10
    Sonstigeevaporate in vacuo

Vorschrift

Combine 1-(3,4,5-trimethoxybenzoyl)-3-(2-(4-(1H-benzimidazol-2-yl-amino)piperidin-1-yl)ethyl)-3-(3,4-dichlorophenyl)pyrrolidine (0.54 g, 0.82 mmol) and dimethylformamide (15 mL). Add sodium hydride (0.07 g, 60% in oil, 1.8 mmol). After 1 hour, add 2-chloroethyl ethyl ether (1 mL). Heat to 100° C. After 18 hours, cool to ambient temperature and dilute the reaction mixture with dichloromethane. Extract three times with water, dry the organic layer over Na2SO4, filter and evaporate in vacuo to give a residue. Chromatograph the residue on silica gel eluting with 25/75/1 methanol/ethyl acetate/triethylamine. Collect the product containing fractions, evaporate in vacuo to give a residue, and chromatograph on silica gel eluting with 20/80/0.5 methanol ethyl acetate/triethylamine to give the title compound: Rf=0.23 (silica gel, 30% methanol/ethyl acetate).

Quelle