Sodium Dichromate → 2,7-Bis(1-oxo-4-(1-piperidyl)butyl)-9H-fluoren-9-one

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Reaction Steps

A solution of 9.0g (0.019 mole) 2,7-bis(4-piperidinobutyryl)fluorene, prepared in Example 7, 7.54g (0.0253 mole) sodium dichromate and 300 ml of glacial acetic acid was stirred and refluxed for one hour. The reaction mixture was evaporated to semi-dryness and made basic using concentrated ammonium hydroxide. The solid which precipitated was filtered, washed with water, and chromatographed on alumina using chloroform as the eluant. The solvent was removed from the fraction collected, leaving a solid residue which was recrystallized three times from chloroform-acetone to yield the desired product. M.P. 168°-170° C, λmaxCHCl3 281, E1cm1% 1579.

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