Phthalic Anhydride → Ammonia

Participants

Reaction Steps

Phthalic anhydride (2.96 g, 0.02 mol, finely ground) and 4-amino-1-[2-(indol-3-yl)ethyl]piperidine (4.86 g, 0.02 mol) were suspended in chloroform (40 cm3) and the suspension stirred at room temperature overnight. The solvent was then evaporated and acetic anhydride (40 cm3) added to the residue. This mixture was heated on a steam bath for 2 hours then the solvent removed in vacuo to give a glassy solid which was dissolved in very dilute aqueous acetic acid. Basification of the solution with 0.880 ammonia gave the title compound as a gum which solidified on trituration with methanol. (4.31 g, 57.8%). A suspension of the base in ethanolic HCl was stirred overnight to give the hydrochloride, mp. 252°-260° after extensive decomposition above 240° C.

Provenance & Evidence