p-Toluidine → HCID 10130194, compound

A reaction container was charged with 1,5-dibromopentane (43 g, 186.6 mmol), sodium carbonate (30 g, 280 mmol) and 100 ml of methanol which were weighed and the mixture was stirred at ambient temperature. Then, p-toluidine (10 g, 93.3 mmol) was dissolved in methanol (50 ml) and the solution was added dropwise to the reaction solution. The reaction solution was heated to 55° C. and stirred for 5 hours. The reaction solution was filtered and the resulting filtrate was concentrated under a reduced pressure. The resulting oily mixture was dissolved in ethyl acetate, which was washed with aqueous saturated sodium bicarbonate by using a separating funnel and extracted with 3% hydrochloric acid. Sodium bicarbonate was added to the water phase with stirring the water phase to neutralize it and then the water phase was extracted with ethyl acetate three times. The resulting ethyl acetate solutions were combined and the combined solution was dried using magnesium sulfate and filtered and the filtrate was concentrated under a reduced pressure and distilled under a reduced pressure to obtain 1-(4-methylphenyl)piperidine (8.2 g, yield: 50.3%).

1. additionthe solution was added dropwise to the reaction solution
2. temperatureThe reaction solution was heated to 55° C.
3. stirringstirred for 5 hours
4. filtrationThe reaction solution was filtered
5. concentrationthe resulting filtrate was concentrated under a reduced pressure
6. dissolutionThe resulting oily mixture was dissolved in ethyl acetate
7. washwhich was washed with aqueous saturated sodium bicarbonate
8. extractionextracted with 3% hydrochloric acid
9. additionSodium bicarbonate was added to the water phase
10. stirringwith stirring the water phase
11. extractionthe water phase was extracted with ethyl acetate three times
12. customthe combined solution was dried
13. filtrationfiltered
14. concentrationthe filtrate was concentrated under a reduced pressure
15. distillationdistilled under a reduced pressure

ORD record

ord-178ce3e1b59e4e649f63a244b85f6ca4

Source dataset

uspto-grants-2005_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06958205B2