HCID 19375088, compound → HCID 19375030, compound

Participants

Reaction Steps

N-(4-(2,2-dimethoxyethyl)phenyl)octanamide (1.11 g, prepared as in example 21) is reduced with lithium aluminum hydride (1.4 equivalents) in refluxing THF (15 ml) to provide 1-(2,2-dimethoxyethyl)-4-(octylamino)benzene as a pale yellow oil after the usual work-up. This material (0.96 g) is dissolved in dichloromethane (10 ml) and treated with acetic anhydride (0.32 ml), triethylamine (0.5 ml) and DMAP (50 mg). The mixture is stirred at room temperature for 4 hr, then washed in turn with 10% aqueous citric acid and saturated sodium bicarbonate. The organic solution is dried, filtered, and concentrated to provide N-(4-(2,2-dimethoxyethyl)phenyl)-N-octylacetamide as a colorless oil (1.05 g). This is condensed with glyoxylic acid by the method of example 2 above, to provide the title compound, mp 103°-105° after recrystallization from dichloromethane-hexane.

Provenance & Evidence