Hydrochloric Acid → HCID 23512694, compound

Participants

Reaction Steps

Benzoyl chloride (900 mg, 6.40 mmol) was added in a single portion to a cooled (0° C.) solution of 1-(3-aminopropyl)-2-(2-methoxyethyl)-6,7,8,9-tetrahydro-1H-imidazo[4,5-c]quinolin-4-amine (1.9 g, 6.26 mmol) and triethylamine (2 mL) in 1-methyl-2-pyrrolidinone (100 mL). When analysis by HPLC indicated that the reaction was complete, it was diluted with diethyl ether (1 L). The product was salted out by adding 3.3 eq. of a 1.0 M solution of hydrochloric acid in diethyl ether. The solid was isolated by filtration and then dissolved in water. The solution was neutralized using solid potassium carbonate and then extracted with dichloromethane. The extract was concentrated under reduced pressure to provide a solid. This material was recrystallized from 1,2-dichloroethane, slurried with diethyl ether, filtered and then dried in a vacuum oven to provide 1.47 g of N-{3-[4-amino-2-(2-methoxyethyl)-6,7,8,9-tetrahydro-1H-imidazo[4,5-c]quinolin-1-yl]propyl}benzamide as a white solid, m.p. 167.8-169.6° C. Analysis: Calculated for C23H29N5O2: % C, 67.05; % H, 7.22; % N, 17.00. Found: % C, 67.17; % H, 7.24; % N, 16.98.

Provenance & Evidence