Chloroacetyl chloride → HCID 178521458, compound

Participants

Reaction Steps

2-[Trans-4-(4-nitro-3-trifluoromethyl-phenylamino)-cyclohexyloxy]-1-{4-[4-(4-trifluoromethyl-benzyloxy)-phenyl]-piperazin-1-yl}-ethanone was prepared using a two-step synthesis. In the first step, 1-chloracetyl-4-[4-(4-trifluoromethyl-benzyloxy)-phenyl]-piperazine (also known as 2-chloro-1-{4-[4-(4-trifluoromethyl-benzyloxy)-phenyl]-piperazin-1-yl}-ethanone) was prepared with a 46% yield from 1-[4-(4-trifluoromethyl-benzyloxy)-phenyl]-piperazine (prepared in accordance with Example 19) 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-(4-trifluoromethyl-benzyloxy)-phenyl]-piperazin-1-yl}-ethanone was prepared from the 1-chloracetyl-4-[4-(4-trifluoromethyl-benzyloxy)-phenyl]-piperazine 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 (10% yield). The structure was confirmed using Protocol II-A. Calculated mass=681; observed mass=681; HPLC retention time=4.75 min.

Provenance & Evidence