Chloroacetyl chloride → HCID 178440755, compound

HRID 1047372Notes

Reaction equation

HRID 1047372 reaction equation
[CH2:1]([C:5]1[CH:10]=[CH:9][C:8]([CH:11]2[CH2:16][CH2:15][N:14]([C:17](=[O:20])[CH2:18]Cl)[CH2:13][CH2:12]2)=[CH:7][CH:6]=1)[CH2:2][CH2:3][CH3:4].C(C1C=CC(C2CCNCC2)=CC=1)CCC.ClCC(Cl)=O.[N+:42]([C:45]1[CH:50]=[CH:49][C:48]([NH:51][C@H:52]2[CH2:57][CH2:56][C@H:55]([OH:58])[CH2:54][CH2:53]2)=[CH:47][C:46]=1[C:59]([F:62])([F:61])[F:60])([O-:44])=[O:43]>>[CH2:1]([C:5]1[CH:10]=[CH:9][C:8]([CH:11]2[CH2:16][CH2:15][N:14]([C:17](=[O:20])[CH2:18][O:58][C@H:55]3[CH2:56][CH2:57][C@H:52]([NH:51][C:48]4[CH:49]=[CH:50][C:45]([N+:42]([O-:44])=[O:43])=[C:46]([C:59]([F:60])([F:61])[F:62])[CH:47]=4)[CH2:53][CH2:54]3)[CH2:13][CH2:12]2)=[CH:7][CH:6]=1)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 4

HCID 6577Chloroacetyl chlorideHCID 13078442HCID 13078442, compoundHCID 66851791HCID 66851791, compoundHCID 178526690HCID 178526690, compound

Product 1

HCID 178440755HCID 178440755, compoundYield 72%

Procedure

1-[4-(4-Butyl-phenyl)-piperidin-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-butyl-phenyl)-piperidine (also known as 1-[4-(4-butyl-phenyl)-piperidin-1-yl]-2-chloroethanone) was prepared with a 72% yield from 4-(4-butyl-phenyl)-piperidine (prepared in accordance with Example 9) and chloroacetyl chloride using the procedure illustrated in Example 4. In the second step, the 1-[4-(4-butyl-phenyl)-piperidin-1-yl]-2-[trans-4-(4-nitro-3-trifluoromethyl-phenylamino)-cyclohexyloxy]-ethanone was prepared from the 1-chloracetyl-4-(4-butyl-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 (36% yield). The structure was confirmed using Protocol II-A. Calculated mass=548; observed mass=548; HPLC retention time=4.92 min.

Workup

  1. customa two-step synthesis

Sources & evidence

ORD record
ord-1343511856c846b49f976513b8204709
Source dataset
uspto-grants-2013_10
Patent number
US08569495B2

Reaction notes

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