Methylamine → 6-Chloro-N-methyl-3-pyridinemethanamine

A mixture of 15.05 g of 2-chloro-5-(chloromethyl) pyridine and 50 ml of acetonitrile was dropwise added to a mixture of 36 g of 40% methylamine aqueous solution and 200 ml of acetonitrile during an hour at room temperature and stirred for an hour and a half. The reaction mixture was concentrated. The resulting residue to which 100 ml of water was added, was neutralized by sodium hydrogen carbonate, saturated with sodium chloride and extracted with dichloromethane (200 ml×2). The organic layer was dried over anhydrous magnesium sulfate, concentrated and purified by a column chromatography [developing solvent: dichloromethane-methanol (4:1)] to afford 8.77 g of 2-chloro-5-(methylaminomethyl)pyridine as a yellowish brown liquid.

1. concentrationThe reaction mixture was concentrated
2. additionThe resulting residue to which 100 ml of water was added
3. extractionextracted with dichloromethane (200 ml×2)
4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
5. concentrationconcentrated
6. custompurified by a column chromatography [developing solvent: dichloromethane-methanol (4:1)]

ORD record

ord-15349f90d5234b6aaef6d84c3387a9b8

Source dataset

uspto-grants-1997_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05633375