Formaldehyde → HCID 58975535, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of (3-{[2-(3-isopropoxy-phenylamino)-ethylamino]-methyl}-phenyl)-piperidin-1-yl-methanone (Example 10; 0.048 g, 0.12 mmol) in CH3CN (10 mL) was added a solution of formaldehyde (0.0029 g, 0.097 mmol) in CH3CN (5 mL), followed by sodium cyanoborohydride (0.006 g, 0.1 mmol) and acetic acid (2 drops), and the resulting solution was stirred at 25° C. for 15 h. The solution was treated with aqueous satd NaHCO3 (20 mL), H2O (20 mL) and EtOAc (30 mL). The aqueous layer was back-extracted with EtOAc (3×40 mL), and the combined organic layers were washed with brine (40 mL), dried (MgSO4) and filtered. The filtrate was concentrated under reduced pressure. The crude residue was purified by preparative TLC (5% CH3OH/CH2Cl2) to provide a tan oil (0.0063 g, 13%). MS (ESI): mass calculated for C25H35N3O2, 409.27; m/z found, 410.2 [M+H]+. 1H NMR (400 MHz, CDCl3): 7.39-7.26 (m, 4H), 7.04 (t, J=8.0 Hz, 1H), 6.26-6.16 (m, 3H), 4.15 (hept, J=6.0 Hz, 1H), 3.71-3.61 (m, 4H), 3.31-3.20 (m, 4H), 2.72 (br s, 2H), 2.26 (br s, 2H), 1.66-1.50 (m, 8H), 1.32 (d, J=6.0 Hz, 6H).

Provenance & Evidence