1,1'-Carbonyldiimidazole → HCID 14390254, compound

A solution of 2-(3-chlorophenyl)-3H-imidazo[4,5-b]pyridine-3-acetic acid (5.76 g, 0.020 mole), 1,1'-carbonyldiimidazole (3.24 g, 0.020 mole), and anhydrous tetrahydrofuran (250 ml) was stirred at room temperature with a stream of nitrogen bubbling through it for 21/2 hrs. The nitrogen flow was stopped and a solution of 3-amino-N-ethylpiperidine (2.56 g, 0.020 mole) in dry tetrahydrofuran (50 ml) was added. The solution was stoppered and stirred at room temperature for 2 hrs. The reaction was concentrated in vacuo and partitioned between ethyl acetate (150 ml) and potassium bicarbonate solution (50 ml). The layers were separated and the organic portion was washed with potassium bicarbonate solution (2×50 ml), water (50 ml), brine (25 ml), dried over sodium sulfate, and concentrated in vacuo. The solid residue (3.4 g) was converted to the hydrochloride salt and twice recrystallized from acetone-tetrahydrofuran-ethanol to give 2.7 g (31%) of a white solid, mp. 275°-276° C. with decomposition.

1. concentrationThe reaction was concentrated in vacuo
2. custompartitioned between ethyl acetate (150 ml) and potassium bicarbonate solution (50 ml)
3. customThe layers were separated
4. washthe organic portion was washed with potassium bicarbonate solution (2×50 ml), water (50 ml), brine (25 ml)
5. dry with materialdried over sodium sulfate
6. concentrationconcentrated in vacuo
7. customtwice recrystallized from acetone-tetrahydrofuran-ethanol

ORD record

ord-a24e9935a86546d28dcccd75eb98cb92

Source dataset

uspto-grants-1990_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04948800