N-Methylaniline → HCID 71613320, compound

Participants

Reaction Conditions

Reaction Steps

Compound 11a (0.20 g, 0.816 mmol) and compound N-methylaniline (0.176 mL, 1.63 mmol) were stirred in acetonitrile (10 mL) for 30 mins and then diisopropylethylamine (0.33 mL, 2.44 mmol) was added dropwise. The reaction was then stirred at 60° C. for 12 hours and monitored by TLC. The reaction mixture was concentrated and treated with formic acid to facilitate purification by column chromatography to isolate compound 11 as a colorless oil (0.12 g, 0.36 mmol, 46% yield). MS (ESI, positive) m/z calcd. for C17H22NO2 [M+H]+: 272.16451, found: 272.16452. 1H NMR (CDCl3, 400 MHz) δ 7.29 (t, J=7.2 Hz, 2H), 6.77-6.83 (m, 7H), 6.10 (bs, 1H), 3.92 (t, J=5.2 Hz, 2H), 3.41 (t, J=7.2 Hz, 2H), 2.97 (s, 3H), 1.70-1.81 (m, 4H).

Provenance & Evidence