Chloroacetyl chloride → HCID 178440995, compound

HRID 1047366Notes

Reaction equation

[C:1]([C:5]1[CH:10]=[CH:9][C:8]([N:11]2[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]2)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].Cl[CH2:18][C:19](Cl)=[O:20].[N+:22]([C:25]1[CH:30]=[CH:29][C:28]([NH:31][C@H:32]2[CH2:37][CH2:36][C@H:35]([OH:38])[CH2:34][CH2:33]2)=[CH:27][C:26]=1[C:39]([F:42])([F:41])[F:40])([O-:24])=[O:23]>>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([N:11]2[CH2:16][CH2:15][N:14]([C:19](=[O:20])[CH2:18][O:38][C@H:35]3[CH2:36][CH2:37][C@H:32]([NH:31][C:28]4[CH:29]=[CH:30][C:25]([N+:22]([O-:24])=[O:23])=[C:26]([C:39]([F:40])([F:41])[F:42])[CH:27]=4)[CH2:33][CH2:34]3)[CH2:13][CH2:12]2)=[CH:9][CH:10]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

Reactant 3

HCID 6577Chloroacetyl chloride

HCID 7817221-(4-tert-Butylphenyl)piperazine

HCID 178526690HCID 178526690, compound

Product 1

HCID 178440995HCID 178440995, compoundYield 92%

Procedure

1-[4-(4-Tert-butyl-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-Tert-butyl-phenyl)-piperazine was prepared with a 92% yield from 1-(4-Tert-butyl-phenyl)-piperazine and chloroacetyl chloride using the procedure illustrated in Example 4. In the second step, the 1-[4-(4-tert-butyl-phenyl)-piperazin-1-yl]-2-[trans-4-(4-nitro-3-trifluoromethyl-phenylamino)-cyclohexyloxy]-ethanone was prepared from the 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 (32% yield). The structure was confirmed using Protocol II-A. Calculated mass=563; observed mass=563; HPLC retention time=4.79 min.

Workup

customa two-step synthesis

Sources & evidence

ORD record: ord-a7d7f9ba85a641a3b0abfeb0e0a71f45
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08569495B2

Reaction notes

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