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 added dropwise to a mixture of 36 g of 40% aqueous methylamine solution and 200 ml of acetonitrile over a period of 1 hour at room temperature and the whole mixture was further stirred for 90 minutes. The reaction mixture was concentrated and the residue was diluted with 100 ml of water, neutralized with sodium hydrogen carbonate, saturated with sodium chloride and extracted with dichloromethane (200 ml×2). The organic solution was dried over anhydrous magnesium sulfate and concentrated and the residue was purified by column chromatography (eluent: dichloromethane-methanol (4:1)) to give 8.77 g of 2-chloro-5-(methylaminomethyl)pyridine as a yellow brown liquid.

1. concentrationThe reaction mixture was concentrated
2. additionthe residue was diluted with 100 ml of water
3. extractionextracted with dichloromethane (200 ml×2)
4. dry with materialThe organic solution was dried over anhydrous magnesium sulfate
5. concentrationconcentrated
6. customthe residue was purified by column chromatography (eluent: dichloromethane-methanol (4:1))

ORD record

ord-6d38b0541e414dc1aff8eb1c13c535c4

Source dataset

uspto-grants-1992_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05084459