Hexamethylenetetramine → 6-Bromo-2-Pyridinemethanamine

2-Bromo-6-bromomethyl-pyridine (2.67 g, 10.63 mmol) was combined with hexamethylenetetramine (3.00 g, 21.30 mmol) in chloroform (50 ml) and the resulting reaction mixture was stirred at reflux for 14 hours. The reaction mixture was then cooled to room temperature and the white solid was collected by filtration. The white solid was suspended in ethanol (50 ml) and concentrated HCl (12 ml) was added. The resulting reaction mixture was stirred at 90° C. for 14 hours. Adjustment of pH to 12 was done by the addition of aq 5N NaOH. The reaction mixture was extracted with dichloromethane several times. The combined organic layers were concentrated to yield the title compound. Spectroscopic data: 1H NMR (300 MHz, CDCl3) δ 3.95 (s, 2H) 7.19-7.28 (m, 2H) 7.62 (t, J=7.82 Hz, 1H).

1. customthe resulting reaction mixture
2. temperatureat reflux for 14 hours
3. filtrationthe white solid was collected by filtration
4. additionconcentrated HCl (12 ml) was added
5. customThe resulting reaction mixture
6. stirringwas stirred at 90° C. for 14 hours
7. extractionThe reaction mixture was extracted with dichloromethane several times
8. concentrationThe combined organic layers were concentrated

ORD record

ord-7e4040e942874d17a44cc10771265da1

Source dataset

uspto-grants-2013_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08557853B2