Pyridine, 4-(2-methoxyethyl)- → 4-(2-Methoxyethyl)piperidine

4-(2-Methoxyethyl)pyridine (9.6 g), in a mixture of ethanol (100 ml) and 2 N hydrochloric acid (30 ml) was hydrogenated over platinum oxide at 50°/50 p.s.i. until uptake of hydrogen ceased. The catalyst was removed by filtration and the solution evaporated in vacuo. The residue was then dissolved in water (50 ml), basified to pH 8 with dilute sodium hydroxide, and extracted with chloroform. The aqueous phase was evaporated in vacuo to give an oil which solidified on cooling. The solid was triturated with ether (60 ml), collected by filtration and dissolved in the minimum quantity of boiling ethyl acetate. The hot solution was filtered and on cooling deposited hygroscopic crystals of 4-(2-methoxyethyl)piperidine (9.9 g), m.p. 108°-110°. The structure was verified by i.r. and n.m.r. spectroscopy.

1. customThe catalyst was removed by filtration
2. customthe solution evaporated in vacuo
3. dissolutionThe residue was then dissolved in water (50 ml)
4. extractionextracted with chloroform
5. customThe aqueous phase was evaporated in vacuo
6. customto give an oil which
7. temperatureon cooling
8. customThe solid was triturated with ether (60 ml)
9. filtrationcollected by filtration
10. dissolutiondissolved in the minimum quantity of boiling ethyl acetate
11. filtrationThe hot solution was filtered
12. temperatureon cooling

ORD record

ord-a5d2f8cea8b442ab88705adfd13cdf3f

Source dataset

uspto-grants-1981_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04289772