Chloroacetyl chloride → HCID 178521458, compound

HRID 1047371Notes

Reaction equation

HRID 1047371 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][CH2:18][C:19]3[CH:24]=[CH:23][C:22]([C:25]([F:28])([F:27])[F:26])=[CH:21][CH:20]=3)=[CH:13][CH:12]=2)[CH2:7][CH2:6]1)=[O:4].FC(F)(F)C1C=CC(COC2C=CC(N3CCNCC3)=CC=2)=CC=1.ClCC(Cl)=O.[N+:58]([C:61]1[CH:66]=[CH:65][C:64]([NH:67][C@H:68]2[CH2:73][CH2:72][C@H:71]([OH:74])[CH2:70][CH2:69]2)=[CH:63][C:62]=1[C:75]([F:78])([F:77])[F:76])([O-:60])=[O:59]>>[N+:58]([C:61]1[CH:66]=[CH:65][C:64]([NH:67][C@H:68]2[CH2:73][CH2:72][C@H:71]([O:74][CH2:2][C:3]([N:5]3[CH2:10][CH2:9][N:8]([C:11]4[CH:16]=[CH:15][C:14]([O:17][CH2:18][C:19]5[CH:24]=[CH:23][C:22]([C:25]([F:28])([F:27])[F:26])=[CH:21][CH:20]=5)=[CH:13][CH:12]=4)[CH2:7][CH2:6]3)=[O:4])[CH2:70][CH2:69]2)=[CH:63][C:62]=1[C:75]([F:76])([F:77])[F:78])([O-:60])=[O:59]

Participants

5

Reactant 4

HCID 6577Chloroacetyl chlorideHCID 585767301-(4-(4-Trifluoromethyl-benzyloxy)-phenyl)-piperazineHCID 668519512-Chloro-1-{4-[4-(4-trifluoromethyl-benzyloxy)-phenyl]-piperazin-1-yl}-ethanoneHCID 178526690HCID 178526690, compound

Product 1

HCID 178521458HCID 178521458, compoundYield 46%

Procedure

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.

Workup

  1. customa two-step synthesis

Sources & evidence

ORD record
ord-e5299edb93824f53ae86ea072dd3b604
Source dataset
uspto-grants-2013_10
Patent number
US08569495B2

Reaction notes

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