Formaldehyde → HCID 67323666, compound

Participants

Reaction Conditions

Reaction Steps

(4-(4-phenylthiazol-2-yl)tetrahydro-2H-pyran-4-yl)methanamine (300 mg, 1.1 mmol) was dissolved in 1,2-dichloroethane (30 mL) and cooled to 0° C. Formaline solution (˜0.1 mL, 35%) was added to the solution, followed by sodiumtriacetoxy borohydride (0.16 g, 0.76 mmol). The reaction mixture was further stirred for 45 min maintaining the same temperature. The reaction mixture was then quenched with 10% NaHCO3 solution and diluted with CH2Cl2. The organic layer was separated, dried over anhydrous Na2SO4, and concentrated under reduced pressure. The residue was purified by column chromatography (silica 60-120 mesh, eluent 10-20% MeOH in CHCl3) to afford N-methyl-1-(4-(4-phenylthiazol-2-yl)tetrahydro-2H-pyran-4-yl)methanamine (120 mg, yield 38%). 1H NMR (300 MHz, CDCl3) δ 7.90-7.88 (m, 2H), 7.48 (s, 1H), 7.44-7.34 (m, 3H), 3.93-3.86 (m, 2H), 3.75-3.67 (ddd, J=12.0 Hz, 8.9 Hz, 3.0 Hz, 2H), 3.01 (s, 2H), 2.49 (s, 3H), 2.36-2.39 (m, 2H), 2.09-2.01 (m, 2H). MS (ESI) m/z: Calculated for C16H20N2OS: 288.13. found: 289.2 (M+H)+.

Provenance & Evidence