Reaktion #9541

Reaktionsgleichung

tert-butyl 4-[2-(4-amino-7-bromo-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl)ethyl]-4-oxidopiperazine-1-carboxylate

Phosphorous trichloride

→

7-bromo-2-ethoxymethyl-1-(2-piperazin-1-ylethyl)-1H-imidazo[4,5-c]quinolin-4-amine dihydrochloride

Ausbeute 84.2%

Lösungsmittel

chloroform

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturto warm to ambient temperature
2. 2
   SonstigeThe chloroform was removed under reduced pressure
3. 3
   workup.DISSOLUTIONthe residue was dissolved in ethanol (150 mL)
4. 4
   workup.ADDITIONHydrogen chloride (21.5 mL of a 3 M solution in ethanol) was added
5. 5
   Temperaturthe reaction was heated
6. 6
   Temperaturat reflux for 25 minutes
7. 7
   Temperaturto cool to room temperature
8. 8
   Sonstigea precipitate formed
9. 9
   Sonstigewas isolated by filtration

Vorschrift

A solution of tert-butyl 4-[2-(4-amino-7-bromo-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl)ethyl]-4-oxidopiperazine-1-carboxylate (8.84 g, 16.1 mmol) in chloroform (400 mL) was cooled to 4° C. Phosphorous trichloride (9.82 mL, 113 mmol) was added dropwise, and the reaction was stirred for 45 minutes at 4° C. Water (one drop) was added to the reaction, which was allowed to warm to ambient temperature. The chloroform was removed under reduced pressure, and the residue was dissolved in ethanol (150 mL). Hydrogen chloride (21.5 mL of a 3 M solution in ethanol) was added, and the reaction was heated at reflux for 25 minutes. The reaction was allowed to cool to room temperature; a precipitate formed and was isolated by filtration to provide 6.86 g of 7-bromo-2-ethoxymethyl-1-(2-piperazin-1-ylethyl)-1H-imidazo[4,5-c]quinolin-4-amine dihydrochloride as a light yellow solid.

Quelle