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

A mixture of 15.05g of 2-chloro-5-(chloromethyl) pyridine and 50ml of acetonitrile was dropwise added to a mixture of 36g of 40% methylamine aqueous solution and 200ml 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 100ml of water was added, was neutralized by sodium hydrogen carbonate, saturated with sodium chloride and extracted with dichloromethane (200ml×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 8.77g of 2-chloro-5(methylaminomethyl)pyridine as a yellowish brown liquid.

1. concentrationThe reaction mixture was concentrated
2. additionThe resulting residue to which 100ml of water was added
3. extractionextracted with dichloromethane (200ml×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-878f7c38d92c42b68745c76ed80dc9d0

Source dataset

uspto-grants-1991_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05034404