反应详情

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 5 mL of benzylamine 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 9:1 mixture of ammoniated chloroform/methanol to provide 42 mg (34%) of the title compound as a white solid: electrospray MS (m/z, relative intensity) 322 ([MH]+).

1. temperatureto reflux under a nitrogen atmosphere
2. extractionextracted with chloroform (3×25 mL)
3. extractionThe combined organic extract
4. dry with materialwas dried over anhydrous magnesium sulfate
5. concentrationconcentrated in vacuo, and flash
6. customchromatographed on neutral silica gel using
7. additiona 9:1 mixture of ammoniated chloroform/methanol