Acetic Acid → HCID 70203387, compound

Participants

Reaction Steps

0.35 g of (2R)-N1 -(7-chloro-quinolin-4-yl)-propane-1,2-diamine (see Example 118) and 0.22g of 4-dimethylamino-benzaldehyde were boiled under reflux in 50 ml of ethanol overnight. After evaporation of the solvent the residue was again taken up in 20 ml of ethanol, 0.05 g of sodium borohydride was added thereto and the mixture was left to react at room temperature overnight. The excess sodium borohydride was then decomposed by the addition of 5 ml of glacial acetic acid and the solvent was evaporated. After the addition of 10 ml of methanol the mixture was again evaporated. Addition of methanol and evaporation were repeated again, whereafter the mixture was purified by chromatography on 30 g of silica gel with a mixture of dichloromethane and methanol in the ratio by volume 10:1. The product-containing fractions were combined and evaporated, and the residue was taken up in 5 ml of ethanol. After the addition of 5 ml of 3N isopropanolic hydrochloric acid the hydrochloride of the product precipitated and was recrystallized from ethanol/diethyl ether.

Provenance & Evidence