Potassium Carbonate → HCID 67547652, compound

Participants

Reaction Steps

Oxalyl chloride (0.540 ml, 0.0062 mol) was added to a solution of 9H-xanthene-9-carboxylic acid (1.16 g, 0.0051 mol) and dimethylformamide (two drops) in 20 ml of CHCl3 (ethanol free) at ECP. The mixture was allowed to warm to room temperature under stirring and maintained 1-h at this temperature. After this time, the reaction mixture was concentrated to dryness in vacuo and the obtained residue was dissolved in CHCl3 (15 ml) and concentrated again. This procedure was repeated two times. The obtained residue was dissolved in CHCl3 and the solution cooled to 0° C. A solution of 0.865 g (0.0062 mol) of (3R)—N-methylquinuclidin-3-amine (Intermediate I-4) in 10 ml of CHCl3 was added. The mixture was allowed to warm to room temperature under stirring. After 4 hours at this temperature, the reaction mixture was treated with K2CO3 (saturated solution) and the aqueous phase was extracted with CHCl3. The organic solutions were combined and washed with K2CO3 (saturated solution) and water, dried over Na2SO4 filtered and concentrated to dryness. The obtained residue was purified by column chromatography (silica gel, CHCl3:NH4OH 99:1→CHCl3:MeOH:NH4OH 98:2:1 as eluent) to yield 900 mg (50%) of the title product.

Provenance & Evidence