1,8-Diazabicyclo(5.4.0)undec-7-ene → 5-Chloro-6-(piperidin-1-yl)-2,3-dihydrobenzofuran

Participants

Reaction Steps

1.2 ml (8.0 mmole) of 1,8-diazabicyclo[5.4.0]-undec-7-ene (DBU) are added at 0° to a solution of 2.50 g (7.8 mmole) of 1-bromo-2-[5-chloro-2-hydroxy-4-(piperidin-1-yl)-phenyl]-ethane in 50 ml of absolute methylene chloride and the whole is then stirred for 3 hours at room temperature. The reaction mixture is washed with saturated sodium chloride solution and the organic phases are combined, dried over sodium sulphate and concentrated in a vacuum rotary evaporator. The residue is chromatographed over silica gel using methylene chloride as eluant. Recrystallisation from petroleum ether yields 5-chloro-6-(piperidin-1-yl)-2,3-dihydrobenzofuran having a melting point of 38°-40°.

Provenance & Evidence