Carbodiimide → HCID 16678875, compound

Participants

Reaction Steps

In a large glass container with a Teflon cap was placed 1-[1-(ethylsulfonyl)-4-isobutylpiperidin-4-yl]methanamine (5) (670 mg, 2.55 mmol). This was dissolved in dichloromethane (50 ml) and PS-carbodiimide resin (5.11 mmol) was then added along with 2-chloro-4-(trifluoromethyl)benzoic acid (688 mg, 3.06 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). The organics were 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-isobutylpiperidin-4-yl]methyl}-4-(trifluoromethyl)benzamide (7) as a white solid. Calculated HRMS 469.1534 Found 469.15333. 1H NMR (300 MHz D6DMSO): δ 8.85 (s, 1 H), 7.95 (s, 1 H), 7.79 (d, J=7.8 Hz, 1 H), 7.60 (d, J=8.1 Hz, 1 H), 3.34 (s, 2 H), 3.21 (s, 4 H), 3.05 (q, J=7.2 Hz, 2 H), 1.75 (m, 1 H), 1.51 (m, 4 H), 1.29 (d, J=4.8 Hz, 2 H), 1.21 (t, J=7.5 Hz, 3 H), 0.94 (s, 3 H), 0.91 (s, 3H).

Provenance & Evidence