Triethylamine → 4-(2,3-dihydro-2-oxo-1H-imidazo[4,5-b]quinolin-7-yloxy)-N-[1-(phenylmethyl)-4-piperidinyl]butanamide

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Reaction Steps

A mixture of 4-[(2,3-dihydro-2-oxo-1H-imidazo-[4,5-b]quinolin-7-yl)oxy]butyric acid (2 g, 7mmol), 4-amino-1-benzylpiperidine (1.59 g, 1.70 mL, 8.4 mmol), triethylamine (1.54 g, 2.12 mL, 15.2 mmol), diphenylphosphoryl azide (2.87 g, 2.25 mL, 10.4 mmol), 4-dimethylaminopyridine (catalytic quantity) and dimethylformamide (40 mL) was stirred at room temperature for 18 hours. The mixture was then diluted with water and the crude free base product collected. After air drying, the free base was suspended in methanol and acidified with a 10% solution of hydrogen chloride in ethanol. The solution was evaporated and the residue dissolved in methanol. Dilution of the methanol solution with diethyl ether gave 4-(2,3-dihydro-2-oxo-1H-imidazo[4,5-b]quinolin-7-yloxy)-N-[1-(phenylmethyl)-4-piperidinyl]butanamide as the hydrated dihydrochloride salt (3.00 g, 80%), mp. 202°-204 C.

Provenance & Evidence