Carbodiimide → HCID 16678876, compound

Participants

Reaction Steps

In a large glass container with a sealable lid was placed 1-[1-(ethylsulfonyl)-4-(tetrahydro-2H-pyran-4-ylmethyl)piperidin-4-yl]methanamine (11, 350 mg, 1.15 mmol). Dichloromethane (50 ml) and PS-carbodiimide resin (474 mg, 2.299 mmol) were added along with 2-chloro-4(trifluoromethyl)benzoic acid (336 mg, 1.495 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-(tetrahydro-2H-pyran-4-ylmethyl)piperidin-4-yl]methyl}-4-(trifluoromethyl)benzamide (12) as a white solid. Calculated HRMS 511.164 Found 511.1649. 1H NMR (300 MHz D6DMSO): δ 8.51 (s, 1 H)), 7.96 (s, 1 H), 7.80 (d, J=8.1 Hz, 1 H), 7.61 (d, J=7.8 Hz, 1 H), 3.77 (d, J=9.3 Hz, 2 H), 3.41 (s, 2 H), 3.32 (m, 2 H), 3.29 (s, 2H), 3.21 (s, 4 H), 3.45 (q, J=9 Hz, 2 H), 1.66 (m, 1 H), 1.61 (m, 2 H), 1.564 (s, 2 H), 1.47 (m, 2 H), 1.30 (d, J=4.5 Hz, 2 H), 1.21 (t, J=7.5 Hz, 3 H).

Provenance & Evidence