Chloroacetyl chloride → HCID 178491993, compound
Reaction equation
Cl[CH2:2][C:3]([N:5]1[CH2:10][CH2:9][N:8]([C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=2)[CH2:7][CH2:6]1)=[O:4].COC1C=CC(N2CCNCC2)=CC=1.ClCC(Cl)=O.[N+:38]([C:41]1[CH:46]=[CH:45][C:44]([NH:47][C@H:48]2[CH2:53][CH2:52][C@H:51]([OH:54])[CH2:50][CH2:49]2)=[CH:43][C:42]=1[C:55]([F:58])([F:57])[F:56])([O-:40])=[O:39]>>[CH3:18][O:17][C:14]1[CH:15]=[CH:16][C:11]([N:8]2[CH2:9][CH2:10][N:5]([C:3](=[O:4])[CH2:2][O:54][C@H:51]3[CH2:52][CH2:53][C@H:48]([NH:47][C:44]4[CH:45]=[CH:46][C:41]([N+:38]([O-:40])=[O:39])=[C:42]([C:55]([F:56])([F:57])[F:58])[CH:43]=4)[CH2:49][CH2:50]3)[CH2:6][CH2:7]2)=[CH:12][CH:13]=1Participants
Procedure
1-[4-(4-Methoxy-phenyl)-piperazin-1-yl]-2-[trans-4-(4-nitro-3-trifluoromethyl-phenylamino)-cyclohexyloxy]-ethanone was prepared using a two-step synthesis. In the first step, 1-chloracetyl-4-(4-methoxy-phenyl)-piperazine (also known as 2-chloro-1-[4-(4-methoxy-phenyl)-piperazin-1-yl)-ethanone) was prepared with a 78% yield from 1-(4-methoxy-phenyl)-piperazine and chloroacetyl chloride using the procedure illustrated in Example 4. In the second step, the 1-[4-(4-methoxy-phenyl)-piperazin-1-yl]-2-[trans-4-(4-nitro-3-trifluoromethyl-phenylamino)-cyclohexyloxy]-ethanone was prepared from the 1-chloracetyl-4-(4-methoxy-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 (24% yield). The structure was confirmed using Protocol II-A. Calculated mass=537; observed mass=537; HPLC retention time=4.05 min.
Workup
- customa two-step synthesis
Sources & evidence
- ORD record
- ord-4c740ab2cba9464a89a9400c553bd36b
- Source dataset
- uspto-grants-2013_10
- Patent number
- US08569495B2
Reaction notes
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