Ammonium Chloride → 1-(4-Nitrophenyl)-2-{4-[2-(4-nitrophenyl)ethyl]piperazin-1-yl}ethanone

HRID 1187129Notes

Reaction equation

HRID 1187129 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][CH:6]=1)=[O:4].Cl.[N+:15]([C:18]1[CH:23]=[CH:22][C:21]([CH2:24][CH2:25][N:26]2[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]2)=[CH:20][CH:19]=1)([O-:17])=[O:16].CCN(C(C)C)C(C)C.[NH4+].[Cl-]>>[N+:11]([C:8]1[CH:9]=[CH:10][C:5]([C:3](=[O:4])[CH2:2][N:29]2[CH2:30][CH2:31][N:26]([CH2:25][CH2:24][C:21]3[CH:20]=[CH:19][C:18]([N+:15]([O-:17])=[O:16])=[CH:23][CH:22]=3)[CH2:27][CH2:28]2)=[CH:6][CH:7]=1)([O-:13])=[O:12]

Participants

5

Reactant 4

HCID 25517Ammonium ChlorideHCID 668402-Bromo-4'-nitroacetophenoneHCID 81531DiisopropylethylamineHCID 666440061-[2-(4-Nitrophenyl)ethyl]piperazine hydrochloride

Product 1

HCID 498013261-(4-Nitrophenyl)-2-{4-[2-(4-nitrophenyl)ethyl]piperazin-1-yl}ethanone

Procedure

2-Bromo-1-(4-nitrophenyl)ethanone (269 mg, 1.10 mmol) was added to a stirred solution of 1-[2-(4-nitrophenyl)ethyl]piperazine hydrochloride (200 mg, 0.736 mmol) followed by Hünig's base, then was stirred at RT for 1 h. The reaction mixture was poured into saturated NH4Cl solution and extracted twice with ethyl acetate. The combined organic layers were washed with water, then brine. The organic layer was dried over MgSO4, filtered, and concentrated. The residue was purified by preparative TLC using 5% MeOH/DCM solvent system to yield 1-(4-nitrophenyl)-2-{4-[2-(4-nitrophenyl)ethyl]piperazin-1-yl}ethanone.

Workup

  1. extractionextracted twice with ethyl acetate
  2. washThe combined organic layers were washed with water
  3. dry with materialThe organic layer was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by preparative TLC

Sources & evidence

ORD record
ord-bd3b112d6e0a4907ba2ebff8f5ff8d94
Source dataset
uspto-grants-2014_03
Patent number
US08673920B2

Reaction notes

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