Carbodiimide → HCID 16678877, compound

Participants

Reaction Steps

In a large glass container with a sealable lid was placed 1-[1-(ethylsulfonyl)-4-(tetrahydrofuran-2-ylmethyl)piperidin-4-yl]methanamine (16, 3.4 g, 11.71 mmol), dichloromethane (50 ml) and PS-carbodiimide resin (35.1 mmol) along with 2-chloro-4-(trifluoromethyl)benzoic acid (3.41 g, 14.05 mmol). The lid was sealed and the bottle was shaken for 0.5 hours. The resin was filtered off and washed with EtOAc (3×25 ml) and the organics concentrated in vacuo to give an off-white solid. The residue was purified by column chromatography on silica gel, eluting with EtOAc/Hexanes to give 2-chloro-N-{[1-(ethylsulfonyl)-4-(tetrahydrofuran-2-ylmethyl)piperidin-4-yl]methyl}-4-(trifluoromethyl)benzamide (17) as a white solid. Calculated HRMS 497.1483 Found 497.1513. 1H NMR (300 MHz CDCl3): δ 7.70 (m, 2 H), 7.59 (d, J=7.8 Hz, 1 H), 3.86 (m, 3 H), 3.68 (q, J=5.7 Hz, 1 H), 3.57 (m, 2 H), 3.38 (m, 2 H), 3.16 (dt, J=10.2 Hz, 1 H), 2.99 (q, J=7.5 Hz, 2 H), 2.00 (m, 1 H), 1.85 (m, 2 H), 1.57 (m, 7 H), 1.38 (t, 7.8 Hz, 3 H.

Provenance & Evidence