Reaktion #76804

Reaktionsgleichung

4′-chlorospiro[1-azabicyclo[2.2.2]octane-3,2′(3′H)-furo[2,3-b]pyridine]

1-methylpiperazine

sodium carbonate

→

title compound

Ausbeute 48.0%

4′-(4-N-Methylpiperazin-1-yl)spiro[1-azabicyclo[2.2.2]octane-3,2′(3′H)-furo[2,3-b]pyridine]

Ausbeute 48.0%

Lösungsmittel

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturto reflux under a nitrogen atmosphere
2. 2
   Extraktionextracted with chloroform (3×25 mL)
3. 3
   ExtraktionThe combined organic extract
4. 4
   Trocknenwas dried over anhydrous magnesium sulfate
5. 5
   Einengenconcentrated in vacuo, and flash
6. 6
   Sonstigechromatographed on neutral silica gel using
7. 7
   workup.ADDITIONa 4:1 mixture of ammoniated chloroform/methanol

Vorschrift

A solution of 97 mg (0.387 mmol) of 4′-chlorospiro[1-azabicyclo[2.2.2]octane-3,2′(3′H)-furo[2,3-b]pyridine] in 1 mL of 1-methylpiperazine was heated to reflux under a nitrogen atmosphere and stirred for 18 hours. Upon cooling to ambient temperature, the diluted with 40 mL of water, basicified with 2 mL of saturated aqueous sodium carbonate and extracted with chloroform (3×25 mL). The combined organic extract was dried over anhydrous magnesium sulfate, concentrated in vacuo, and flash chromatographed on neutral silica gel using a 4:1 mixture of ammoniated chloroform/methanol to provide 59 mg (48%) of the title compound as an amber oil: electrospray MS (m/z, relative intensity) 315 ([MH]+).

Quelle