Hydrochloric Acid → 1-Methyl-4-(2-nitrophenyl)piperidin-4-ol

Participants

Reaction Conditions

Reaction Steps

To a solution of 19.3 g of 2-bromonitrobenzene in 480 ml of anhydrous tetrahydrofuran cooled to -100° C., 79 ml of 1,6M solution of n-Buli in hexane are dropped under N2. After two hours 10.9 g of 1-methyl-4-piperidone are added and the resulting mixture is stirred eight hours at -100° C. Then 1N hydrochloric acid is added at 0° C. to acidify to pH 2 and the solution is extracted with hexane. The aqueous phase is brought to pH 10 and extracted with ethyl ether. Evaporation of the extracts gives 8.95 g of 1-methyl-4(2-nitrophenyl)-4-hydroxypiperidine, m.p. 166°-167°.

Provenance & Evidence