Acetic Acid → HCID 68569693, compound

Temperature

120 °C

A 500 mL 4-necked flask with mechanical stirrer, N2 inlet and reflux condenser is charged with 9.3 g (37.2 mmol) 1-methyl-4-(3-nitro-benzyloxy)-piperidine and 150 mL of acetic acid. Under efficient stirring 13.14 g (223 mmol) of iron powder is added and the mixture heated in an oil bath. At around 90 to 100° C. an exothermic reaction starts. The heating is interrupted for about 15 min until the exothermic reaction ceases and then the mixture is re-immersed into the oil bath and heated for 1 h at 120° C. The mixture is transferred to a round-bottomed flask and the solvent removed under reduced pressure. The residue is taken up in 1N HCl and washed with ethyl acetate (3×200 mL). The aqueous phase is treated with sodium carbonate until PH 9-10. The voluminous precipitate is removed by filtration through Celite and the solid washed extensively with ethyl acetate. The aqueous filtrate and the ethyl acetate washings are separated and the aqueous phase extracted with ethyl acetate. The organic phase is washed with brine, dried with sodium sulfate and evaporated. According to the H-NMR the residue is composed of a 1:1 mixture of the desired aniline and the corresponding acetanilide. The mixture is therefore dissolved in 50 mL of ethanol and treated with 50 mL of 2N NaOH. The resulting mixture is heated 20 h under reflux. After cooling the ethanol is distilled off and the remaining aqueous phase extracted with dichloromethane (2×150 mL). The organic phases are washed with brine, dried with potassium carbonate and evaporated. 3-(1-Methyl-piperidin-4-yloxymethyl)-phenylamine is obtained as a brown viscous oil and used without further purification. HPLC: 7.54 (System X2); [M+H]+221.0.

1. temperatureA 500 mL 4-necked flask with mechanical stirrer, N2 inlet and reflux condenser
2. additionis added
3. temperaturethe mixture heated in an oil bath
4. customAt around 90 to 100° C. an exothermic reaction
5. customThe heating is interrupted for about 15 min until the exothermic reaction ceases
6. customThe mixture is transferred to a round-bottomed flask
7. customthe solvent removed under reduced pressure
8. washwashed with ethyl acetate (3×200 mL)
9. additionThe aqueous phase is treated with sodium carbonate until PH 9-10
10. customThe voluminous precipitate is removed by filtration through Celite
11. washthe solid washed extensively with ethyl acetate
12. customThe aqueous filtrate and the ethyl acetate washings are separated
13. extractionthe aqueous phase extracted with ethyl acetate
14. washThe organic phase is washed with brine
15. dry with materialdried with sodium sulfate
16. customevaporated
17. additionis composed of a 1:1 mixture of the desired aniline
18. dissolutionThe mixture is therefore dissolved in 50 mL of ethanol
19. additiontreated with 50 mL of 2N NaOH
20. temperatureThe resulting mixture is heated 20 h
21. temperatureunder reflux
22. temperatureAfter cooling the ethanol
23. distillationis distilled off
24. extractionthe remaining aqueous phase extracted with dichloromethane (2×150 mL)
25. washThe organic phases are washed with brine
26. dry with materialdried with potassium carbonate
27. customevaporated

ORD record

ord-34d59a9de2304e9ba36132df665861b3

Source dataset

uspto-grants-2010_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07691855B2