Chloroacetyl chloride → HCID 178521455, compound

Participants

Reaction Steps

2-[Trans-4-(4-nitro-3-trifluoromethyl-phenylamino)-cyclohexyloxy]-1-[4-(4-phenoxy-phenyl)-piperidin-1-yl]-ethanone was prepared using a two-step synthesis. In the first step, 1-chloracetyl-4-(4-phenoxy-phenyl)-piperidine (also known as 2-chloro-1-[4-(4-phenoxy-phenyl)-piperidin-1-yl]-ethanone) was prepared with a 74% yield from 4-(4-phenoxy-phenyl)-piperidine (prepared in accordance with Example 8) and chloroacetyl chloride using the procedure illustrated in Example 4. In the second step, the 2-[trans-4-(4-nitro-3-trifluoromethyl-phenylamino)-cyclohexyloxy]-1-[4-(4-phenoxy-phenyl)-piperidin-1-yl]-ethanone was prepared from the 1-chloracetyl-4-(4-phenoxy-phenyl)-piperidine and trans-4-(4-nitro-3-trifluoromethyl-phenylamino)-cyclohexanol (prepared in accordance with Example 5) using the procedure illustrated in Example 11. This afforded the product as a yellow solid (14% yield). The structure was confirmed using Protocol I-A. Calculated mass=598; observed mass=598; HPLC retention time=4.81 min.

Provenance & Evidence