Morpholine → 2-[3-Chloro-4-(2-morpholin-4-ylethyl)phenyl]-1,3-benzoxazole

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Reaction Steps

The crude aldehyde was treated with NaCNBH3 and morpholine in MeOH/CH2Cl2 (2 mL). The crude mixture was adsorbed onto silica gel and purified by automated flash chromatography using an EtOAc/hexanes gradient to afford the desired 2-[3-chloro-4-(2-morpholin-4-ylethyl)phenyl]-1,3-benzoxazole: 1H NMR (CDCl3, 300 MHz) δ 8.26–8.25 (d, 1H), 8.09–8.06 (m, 1H), 7.79–7.74 (m, 1H), 7.43–7.34 (m, 3H), 3.78–3.75 (m, 4H), 3.05–3.00 (m, 2H), 2.68–2.59 (m, 6H). MS (ESI) 343 (M+H)+.

Provenance & Evidence