Methyl iodide → N-methyl-1-(1-methyl-1H-imidazol-2-yl)piperidin-4-amine

A solution of iodomethane (0.22 ml, 3.4267 mmol, 1.1 eq) in methanol (5 ml) was added dropwise over a period of 5 min to a solution of benzyl methyl(1-(methylcarbamothioyl)-piperidin-4-yl)carbamate (1 g, 3.115 mmol, 1 eq) in methanol (10 ml). Stirring was then carried out for 20 h at room temperature. When the reaction was complete according to TLC monitoring, the reaction mixture was concentrated under reduced pressure. The residue was taken up in pyridine (15 ml); aminoacetaldehyde-diethylacetal (455 mg, 3.4267 mmol, 1.1 eq) was added and refluxing was carried out for 10 h. The reaction mixture was concentrated under reduced pressure, 2 N HCl solution (20 ml) was added, and the mixture was refluxed for 5 h. The reaction mixture was concentrated under reduced pressure and dried by removal of toluene by distillation. The crude product was used in the next stage without being purified further. Yield: 1.1 g (5.67 mmol)

1. concentrationthe reaction mixture was concentrated under reduced pressure
2. temperaturerefluxing
3. waitwas carried out for 10 h
4. concentrationThe reaction mixture was concentrated under reduced pressure, 2 N HCl solution (20 ml)
5. additionwas added
6. temperaturethe mixture was refluxed for 5 h
7. concentrationThe reaction mixture was concentrated under reduced pressure
8. dry with materialdried by removal of toluene by distillation
9. customwithout being purified further

ORD record

ord-620b30101daf4ff68d1a286dc3776259

Source dataset

uspto-grants-2014_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08680159B2