Methyl iodide → HCID 22139640, compound

To a cold (ice-water bath) solution of 4-picolylamine (1070 gr, 9.9 mol) in methanol (3 l) was added dropwise acetic anhydride (1400 gr, 13.7 mol). During addition the reaction temperature was kept between 10 and 30° C. When the addition of the reagent was complete the reaction mixture was left overnight at room temperature. Iodomethane (800 ml, 24.8 mol) was added to the reaction mixture which was cooled with water bath, under nitrogen atmosphere. During addition the reaction temperature was kept below 25° C. When the addition was complete, the reaction mixture was protected from light and left at room temperature overnight The excess iodomethane was evaporated, crystallization was induced, the reaction mixture was cooled (ice bath) and isopropanol (1.5 l) was added. The reaction mixture was left at −30° C. overnight, the precipitate was filtered off, washed with isopropanol and dried. 4-(Acetaminomethyl)-1-methyl-pyridinium iodide (2043 gr, 7 mol) was obtained as yellow powder (71% yield). 1H-NMR (D2O) δ 2.10 (s, CH3CO), 4.32 (s, CH3N+), 4.63 (s, CH2NHCO), 7.89 (d, j=6.6 Hz, 2H), 8.67 (d, j=6.6 Hz, 2H) ppm.

1. additionDuring addition the reaction temperature
2. customwas kept between 10 and 30° C
3. additionWhen the addition of the reagent
4. temperaturewas cooled with water bath, under nitrogen atmosphere
5. additionDuring addition the reaction temperature
6. customwas kept below 25° C
7. additionWhen the addition
8. customwas evaporated
9. customcrystallization
10. temperaturethe reaction mixture was cooled (ice bath) and isopropanol (1.5 l)
11. additionwas added
12. waitThe reaction mixture was left at −30° C. overnight
13. filtrationthe precipitate was filtered off
14. washwashed with isopropanol
15. customdried

ORD record

ord-ca82a778b30346b69102abe4da54eaf0

Source dataset

uspto-grants-2008_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07439251B2