Dimethylformamide → HCID 18474278, compound

Participants

Reaction Steps

To 40 mg (0.109 mmol) of 1-[(2-chlorophenoxy)methyl]-3-[(piperidin4-yl)methoxy]benzene hydrochloride as prepared in the preceding step, in 1 mL of N,N-dimethylformamide containing 100 μL (0.908 mmol) of N,N-diisopropylethylamine was added 40 mg (0.325 mmol) of ethyl acetimidate hydrochloride. The reaction mixture was stirred at ambient temperature for 3 days. The reaction mixture was concentrated in vacuo and the residue was quenched with 1 N sodium hydroxide, extracted into methylene choride, dried (K2CO3), and concentrated. The residue was dissolved with 1 mL of methylene chloride and then treated with 500 μL of glacial acetic acid. The solution was then applied directly to preparative thin layer chromatography using methylene chloride/methanol/glacial acetic (83:15:2) as developing solvent to provide 33.8 mg of the title compound as a gum. 1H-NMR (300 MHz, DMSO-d6) δ 7.45 (dd, 1 H, J=1.5, 7.9 Hz), 7.27-7.34 (m, 2 H), 7.20-7.23 (dd, 1 H, J=1.4, 8.3 Hz), 6.89-7.04(m, 4 H), 5.76 (s, 2 H), 4.07 (d, 2H, J=14 Hz), 3.87 (d, 2 H, J=6.2 Hz), 3.05 (t, 2 H, J=13 Hz), 2.22 (s, 3 H), 2.05-2.13 (m, 1 H), 1.85 (d, 2 H), 1.71 (br s , 3 H), and 1.18-1.38 (m, 2 H). Mass spectrum (MALDI-TOF; α-cyano4-hydroxycinnamic acid matrix matrix) calcd. for C21H25N2O2: 373.2 (M+H). Found: 373.0.

Provenance & Evidence