Methylamine → Methyl(2-pyridylmethyl)amine

A solution of 2-picolinaldehyde (107.11 g, 1 mol, a severe irritant) in 100 mL of methanol was added to 50 mL of methylamine, and the solution was shaken under N2 for 2 hours. Pre-wetted 10% Pd/C (2.5 g) in 20 mL MeOH was added to the first solution, and the mixture was shaken under 4 arm of H2 for 5 hours. The solution was filtered, the filter cake washed with methanol (2×100 mL), and the solution was filtered through a nylon membrane filter and concentrated in vacuo. Toluene was added, and the solution was concentrated in vacuo to afford 122 g of the title product as an orange oil; bp 80°-82° C.@8 mm Hg. NMR (CDCl3) δ:2.00 (bs,1H), 2.49 (s,3H), 3.88 (s,2H), 7.18 (m, 1H), 7.32 (d,1H), 7.65 (dt,1H), 8.56 (m, 1H).

1. stirringthe mixture was shaken under 4 arm of H2 for 5 hours
2. filtrationThe solution was filtered
3. washthe filter cake washed with methanol (2×100 mL)
4. filtrationthe solution was filtered through a nylon membrane
5. filtrationfilter
6. concentrationconcentrated in vacuo
7. additionToluene was added
8. concentrationthe solution was concentrated in vacuo

ORD record

ord-acfe68b6c00a4a0b897b45c1fb776bcd

Source dataset

uspto-grants-1994_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05362912