Acetic Anhydride → N-{[4-(4-[(1-isopropylpiperidin-4-yl)oxy]phenyl)tetrahydro-2H-pyran-4-yl]methyl}-acetamide

Participants

Reaction Steps

To a stirred solution of (4-{4-[(1-isopropylpiperidin-4-yl)oxy]phenyl}tetrahydro-2H-pyran-4-yl)methylamine (250 mg, 0.753 mmol) and triethylamine (200 μl. 1.88 mmol) in dichloromethane (2 ml) was added dropwise acetic anhydride (78 μl, 0.828 mmol). Reaction left at ambient temperature until reaction complete. Dichloromethane (10 ml) added to the reaction, the organic phase extracted with saturated NaHCO3 (3×10 ml). Organic washings were dried over Na2SO4 and concentrated in vacuo to give the title compound as an oil (203 mg, 72%). 1H NMR (400 MHz, CDCl3) δ 7.19 (d, 2H), 6.94 (d, 2H), 4.95-5.02 (broad, 1H), 4.24-4.38 (m, 1H), 3.79-3.88 (m, 2H), 3.52-3.64 (m, 2H), 3.45 (d, 2H), 2.70-2.88 (m, 3H), 2.36-2.45 (m, 2H), 1.98-2.10 (m, 4H), 1.78-1.90 (m, 7H), 1.05 (d, 6H).

Provenance & Evidence