4-Methylphthalic anhydride → HCID 20568895, compound

Participants

Reaction Steps

4-Amino-1-[2-(indol-3-yl)ethyl]piperidine (1.22 g, 5 mmol) was dissolved in warm methyl cyanide (50 cm3) and a solution of 4-methylphthalic anhydride (0.81 g, 5 mmol) in methyl cyanide (10 cm3) was added dropwise with stirring to precipitate a white solid. The suspension was stirred overnight then the solid collected and heated in acetic anhydride (40 cm3) for 2 hours on a steam bath. The acetic anhydride was evaporated. The residue was dissolved in very dilute aqueous acetic acid and the solution basified by addition of conc. ammonia to give a gum. The mother liquor was decanted and the gum recrystallised from ethanol to give crystals of the title compound (0.53 g, 27.3%).

Provenance & Evidence