Potassium Hydroxide → 3-Pyrrolidinecarboxamide, 2,2,5,5-tetramethyl-

Participants

Reaction Steps

3,5-Dibromo-4-oxo-2,2,6,6-tetramethylpiperidine (II, 30 gm) was added slowly, with stirring, to ammonium hydroxide (500 mL). When the solid is dissolved, potassium hydroxide is added, which results in the precipitation of (III). After filtering the solid, additional potassium hydroxide is added to the remaining solution until the precipitation of more material no longer is observed. The precipitates are combined, dried and recrystallized from benzene, giving a white solid (III, 10 gm, 68%) mp 176°-178° C. (lit ref. [1, except pg. 204] mp 180°-181° C). Both I.R. and NMR confirm the structure of (III).

Provenance & Evidence