4-Pyridinemethanamine,N,2-dimethyl-(9CI) synthesis

Yield:165558-79-2 68%

Reaction Conditions:

in aqueous HBr;dichloromethane;acetonitrile;

Steps:

5 Preparation of Methyl-(2-methyl-pyridin-4-ylmethyl)-amine

Preparation of Methyl-(2-methyl-pyridin-4-ylmethyl)-amine A stirred solution of 0.86 g (6.98 mmol) of 2-methyl-4-hydroxymethylpyridine (R. B. Katz et al., Synthetic Communications, 19, 1989, 317-325) in 48% aqueous HBr was heated at reflux for four days. The reaction mixture was cooled and added dropwise to 20 ml of 40% aqueous methylamine. The volatiles were removed under reduced pressure, and the residue was slurried in CH₂ Cl₂ and then filtered. The filter cake was washed with CH₂ Cl₂, EtOAc, CH₃ CN, and 10% MeOH in CH₃ CN. The filtrate was concentrated, and the residue was flash chromatographed on silica, eluding CH₂ Cl₂:NH₃ -saturated MeOH (9:1). Consequently, 0.65 g (68% yield) of methyl-(2-methyl-pyridin-4-ylmethyl)-amine (39) was obtained as a colorless liquid. IR (neat) 3368 (broad), 1638, 1609, 1562, 1451, 1406 cm^-1. ¹ H NMR (CDCl₃) δ: 2.45 (s,3H), 2.54 (s,3H), 3.73 (s,2H), 7.05 (d,1H,J=5.1 Hz), 7.13 (s,1H), 8.42 (d,1H,J=5.1 Hz). Anal. calc. for C₈ H₁₂ N_2.0.45H2 O: C, 66.58; H, 9.01; N, 19.41. Found: C, 66.49; H, 8.73; N, 19.38. Anal calc. for C₈ H₁₂ N₂, M⁺: 136.1000. Found: 136.0998.

References:

US5498727,1996,A