Acetaldehyde → HCID 20332939, compound

Participants

Reaction Steps

4.78 ml of glacial acetic acid are added dropwise to the ice-cooled mixture of 7.6 g of 3-(2-isopropylaminopropyl)-4-(4-methoxyphenyl)-1,5,6,7-tetrahydro-2H-azepinone, 13.3 ml of acetaldehyde, 4.5 g of sodium cyanoborohydride and 90 ml of acetonitrile. The mixture is stirred at room temperature for 90 minutes, cooled in an ice-bath, acidified to pH=1 with concentrated hydrochloric acid and evaporated. The residue is taken up in 150 ml of water, the solution washed with diethyl ether, filtered, basified with 3 N aqueous sodium hydroxide and extracted with diethyl ether. The extract is dried, evaporated, the residue crystallized from petroleum ether and further purified by suspension in hexane, to yield the 3-[2-(N-isopropyl-N-ethylamino)-propyl]-4-(4-methoxyphenyl)-1,5,6,7-tetrahydro-2H-azepinone melting at 64°-66°.

Provenance & Evidence