Hydrochloric Acid → HCID 22137314, compound

Participants

Reaction Steps

To a solution of crude 2,4,6-trichloro-N-[4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-N-[3-(tetrahydro-pyran-2-yloxy)-benzyl]-benzamide (0.076 g, 0.13 mmol) prepared in Step A in 0.5 mL methanol was added HCl (0.78 mL of a 4.0M solution in 1,4-dioxane, 3.12 mmol) and triethylsilane (0.20 mL, 1.30 mmol). The reaction mixture was stirred at room temperature for 24 hr. Saturated aqueous sodium bicarbonate was added and the aqueous solution was washed with methylene chloride. The organic layer was dried (magnesium sulfate) and concentrated. The residue was purified by preparative TLC (1.0 mm silica gel layer, eluting with 10% methanol/methylene chloride) to afford 0.022 g of 2,4,6-trichloro-N-(3-hydroxy-benzyl)-N-[4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-benzamide. 1H NMR (CDCl3) δ 7.13 (s, 2H), 7.10–7.05 (m, 1H), 7.03 (d, 2H, J=12.0 Hz), 6.79–6.67 (m, 3H), 6.58 (d, 2H, J=11.6 Hz), 4.94 (s, 2H), 4.17–4.13 (m, 2H), 3.15 (bs, 2H), 2.99 (bs, 4H), 1.94 (bs, 4H).

Provenance & Evidence