Hydrochloric Acid → N-Methyl-5-(3-pyridinyl)-2-furanmethanamine

Participants

Reaction Steps

To a solution 23 (104 mg, 0.60 mmol) was added a solution of methylamine (2.0 M, 1.8 mL, 3.6 mmol) in anhydrous CH3OH, a solution of HCl (4.0 M, 0.3 mL, 1.2 mmol) in anhydrous 1,4-dioxane and sodium cyanoborohydride (38 mg, 0.6 mmol). The flask was purged with argon and stirred under an atmosphere of argon at room temperature for 48 h. The solution was adjusted to pH 2 with conc. HCl and the solvent was removed in vacuo. The residue was dissolved in water, washed with Et2O (3×10 mL), adjusted to pH 10 with NaOH(aq) (10 N), extracted with Et2O (3×20 mL), dried (Na2SO4), filtered and the solvent was removed in vacuo. The crude material was chromatographed on silica gel (CH3OH/CHCl3, 10/90, Rf=0.1) to afford the title compound 41 (94 mg, 84% yield) as a yellow oil: 1H NMR (CDCl3) δ 8.89 (m, 1H), 8.46 (m, 1H), 7.91 (m, 1H), 7.28 (m, 1H), 6.67 (d, J=3.2 Hz, 1H), 6.31 (d, J=3.2 Hz, 1H), 3.82 (s, 2H), 2.49 (s, 3H), 2.14 (br s, 1H); LRMS (ESI) m/z calcd for C11H13N2O [M+H]+ 189. found 189; m/z calcd for C10H8NO [M−NH(CH3)]+ 158. found 158; HRMS (ESI) m/z calcd for C11H13N2O [M+H]+ 189.1028. found 189.1041; HPLC>95% (tR=8.74 min, 60 (A):40 (B): 0.02 (C); tR=3.69 min, 60 (A):40 (B): 0.07 (C)).

Provenance & Evidence