Reaktion #164553

Reaktionsgleichung

1,4-diazabicyclo[3.2.2]nonane dihydrochloride

5-fluoro-N-(2-(isopropylamino)-2-oxoethyl)-2-nitrobenzamide

Intermediate 2A

5-fluoro-N-(2-(isopropylamino)-2-oxoethyl)-2-nitrobenzamide

potassium carbonate

→

5-(1,4-diazabicyclo[3.2.2]nonan-4-yl)-N-(2-(isopropylamino)-2-oxoethyl)-2-nitrobenzamide

Ausbeute 69.0%

Lösungsmittel

acetonitrile

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe resulting suspension was heated
2. 2
   FiltrationThe reaction mixture was filtered
3. 3
   Einengenconcentrated
4. 4
   workup.ADDITIONSample was diluted in methanol (100 mL)
5. 5
   Sonstigesplit between two 20 g SCX cartridges
6. 6
   SonstigePurification
7. 7
   Sonstigeby SCX and evaporation to dryness

Vorschrift

To a solution of 5-fluoro-N-(2-(isopropylamino)-2-oxoethyl)-2-nitrobenzamide (Intermediate 2A) (7.39 g, 26.1 mmol) in acetonitrile (240 mL) was added potassium carbonate (14.6 g, 104 mmol) followed by 1,4-diazabicyclo[3.2.2]nonane dihydrochloride (5.45 g, 27.4 mmol). The resulting suspension was heated to reflux at 96° C. overnight. The reaction mixture was filtered and concentrated. Sample was diluted in methanol (100 mL) and split between two 20 g SCX cartridges. Purification by SCX and evaporation to dryness afforded 5-(1,4-diazabicyclo[3.2.2]nonan-4-yl)-N-(2-(isopropylamino)-2-oxoethyl)-2-nitrobenzamide (7.0 g, 18.0 mmol).

Quelle