Hydrochloric Acid → 8-[3-(4-piperidinyl)propanoyl]1,2,5,6-tetrahydro-4H-pyrrolo[3,2,1-ij]quinolin-4-one

Participants

Reaction Conditions

Reaction Steps

8-[3-(1-acetyl-4-piperidinyl)-1-oxopropyl]-1,2,5,6-tetrahydro-4H-pyrrolo[3,2,1-ij]quinoline-4-one (10 g, 28.2 mmol) and 2 N hydrochloric acid (50 mL) were stirred at about 90° C. for 8 hours. After cooled to about 25° C., toluene (30 mL) was added to the reaction mixture, the layers were separated, and 30% aqueous sodium hydroxide solution (16 mL) was added to the aqueous layer to adjust pH to 13.8. A mixture of toluene-acetonitrile (1:1) (50 mL) was added thereto, and the layers were separated. A mixture of toluene-acetonitrile (1:1) (50 mL) was added to aqueous layer, and the layers were separated. The organic layers were combined, 30% brine (30 mL) was added, and the layers were separated. The organic layer was concentrated under reduced pressure to obtain 8.55 g (yield 92.5%) of the desired compound as a solid.

Provenance & Evidence