Chloroacetyl chloride → HCID 178521455, compound

HRID 1047374Notes

Reaction equation

HRID 1047374 reaction equation
Cl[CH2:2][C:3]([N:5]1[CH2:10][CH2:9][CH:8]([C:11]2[CH:16]=[CH:15][C:14]([O:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[CH:13][CH:12]=2)[CH2:7][CH2:6]1)=[O:4].O(C1C=CC(C2CCNCC2)=CC=1)C1C=CC=CC=1.ClCC(Cl)=O.[N+:48]([C:51]1[CH:56]=[CH:55][C:54]([NH:57][C@H:58]2[CH2:63][CH2:62][C@H:61]([OH:64])[CH2:60][CH2:59]2)=[CH:53][C:52]=1[C:65]([F:68])([F:67])[F:66])([O-:50])=[O:49]>>[N+:48]([C:51]1[CH:56]=[CH:55][C:54]([NH:57][C@H:58]2[CH2:63][CH2:62][C@H:61]([O:64][CH2:2][C:3]([N:5]3[CH2:10][CH2:9][CH:8]([C:11]4[CH:16]=[CH:15][C:14]([O:17][C:18]5[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=5)=[CH:13][CH:12]=4)[CH2:7][CH2:6]3)=[O:4])[CH2:60][CH2:59]2)=[CH:53][C:52]=1[C:65]([F:66])([F:67])[F:68])([O-:50])=[O:49]

Participants

5

Reactant 4

HCID 6577Chloroacetyl chlorideHCID 110759844-(4-Phenoxyphenyl)piperidineHCID 66851883HCID 66851883, compoundHCID 178526690HCID 178526690, compound

Product 1

HCID 178521455HCID 178521455, compoundYield 74%

Procedure

2-[Trans-4-(4-nitro-3-trifluoromethyl-phenylamino)-cyclohexyloxy]-1-[4-(4-phenoxy-phenyl)-piperidin-1-yl]-ethanone was prepared using a two-step synthesis. In the first step, 1-chloracetyl-4-(4-phenoxy-phenyl)-piperidine (also known as 2-chloro-1-[4-(4-phenoxy-phenyl)-piperidin-1-yl]-ethanone) was prepared with a 74% yield from 4-(4-phenoxy-phenyl)-piperidine (prepared in accordance with Example 8) 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-phenoxy-phenyl)-piperidin-1-yl]-ethanone was prepared from the 1-chloracetyl-4-(4-phenoxy-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 (14% yield). The structure was confirmed using Protocol I-A. Calculated mass=598; observed mass=598; HPLC retention time=4.81 min.

Workup

  1. customa two-step synthesis

Sources & evidence

ORD record
ord-2e45a9dac9a746f59d9480c5ec336e67
Source dataset
uspto-grants-2013_10
Patent number
US08569495B2

Reaction notes

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