4-(Morpholinomethyl)aniline → HCID 68195256, compound

Participants

Reaction Steps

A mixture of Example 1E (0.060 g, 0.167 mmol) and 4-(morpholinomethyl)aniline (0.051 g, 0.267 mmol) was heated in a capped vial at 90° C. for 1 hour. The crude material was purified by HPLC (see protocol in Example 1F). The TFA salt was treated with saturated aqueous NaHCO3 and extracted into ethyl acetate. The organic layer was dried over MgSO4, filtered, concentrated, and purified on a 12 g column using the ISCO Companion flash system eluting with methanol/ethyl acetate (5:95 to 10:90) to provide the title compound. 1H NMR (400 MHz, CD3OD) δ 2.56-2.39 (m, 4H), 3.54 (s, 2H), 3.73-3.67 (m, 4H), 7.05 (d, J=1.9 Hz, 1H), 7.43-7.36 (m, 2H), 7.61-7.52 (m, 3H), 7.70-7.67 (m, 1H), 7.80-7.73 (m, 2H), 7.86 (s, 1H), 9.15 (s, 1H). MS (ESI+) m/z 488.0 (M+H)+.

Provenance & Evidence