Sodium Hydroxide → HCID 23149968, compound

Participants

Reaction Conditions

Reaction Steps

3-Bromo-N,N-dimethylaniline (Aldrich Co., 1.24 g) was dissolved in tetrahydrofuran (18 ml) and the mixture was cooled to −78° C. An n-butyllithium hexane solution (2.6 M, 3.0 ml) was added to the solution and the mixture was stirred for min. 1-(tert-Butoxycarbonyl)-4-piperidone (1.0 g) was added thereto, and the mixture was gradually warmed to room temperature. After completion of the reaction, a saturated aqueous ammonium chloride solution was added, and the mixture was extracted with diethyl ether. The organic layer was dried and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (elution solvent: hexane:ethyl acetate (5:1-2:1)). 10% Aqueous sulfuric acid (5 ml) and 1,4-dioxane (5 ml) were added to the intermediate, and the mixture was stirred with heating at 70° C. for 3 hr. After completion of the reaction, the mixture was cooled to 0° C. A 1N aqueous sodium hydroxide solution was added, and the mixture was extracted with ethyl acetate. The organic layer was dried and the solvent was evaporated under reduced pressure to give 4-[3-(dimethylamino)phenyl]-1,2,3,6-tetrahydropyridine (119 mg, yield 10%).

Provenance & Evidence