3-Methoxybenzaldehyde → 3-[1-(3-methoxybenzyl)piperidin-4-yl]-4-(3-hydroxyphenyl)-3,4-dihydro-2(1H)-quinazolinone

Participants

Reaction Steps

To a solution of 1.3 g (2.44 mmol) of 3-[1-(3-methoxybenzyl)piperidin-4-yl]-4-(3-benzyloxyphenyl)-3,4-dihydro-2(1H)-quinazolinone in 100 mL of methanol were added 504 mg (8 mmol) of ammonium formate and 50 mg of 10 palladium-carbon, and the mixture was heated under reflux for 8 hours. After being cooled, the reaction mixture was filtered through cerite, and the filtrate was concentrated in vacuo. The residue was dissolved in 50 mL of methanol, and 1.33 g (9.76 mmol) of m-anisaldehyde and 613 mg (9.76 mmol) of sodium cyanoborohydride were added to the solution. The mixture was stirred for 12 hours at ambient temperature. The reaction mixture was concentrated in vacuo, diluted with water, then adjusted to pH 10 with aqueous ammonia and extracted with chloroform. The organic layer separated was dried on potassium carbonate and concentrated in vacuo. The residue was purified by means of column chromatography (silica gel, 1:9 methanol:chloroform) to give 810 mg (1.83 mmol) of the title compound.

Provenance & Evidence