Hydroquinone → 2-(2-chloro-5-methoxy-4-nitrophenyl)-N-(4-(4-methylpiperazin-1-yl)benzyl)ethanamine

HRID 1019764Notes

Reaction equation

HRID 1019764 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[C:5]([O:11][CH3:12])=[CH:4][C:3]=1[CH:13]=[CH2:14].[CH3:15][N:16]1[CH2:21][CH2:20][N:19]([C:22]2[CH:29]=[CH:28][C:25]([CH2:26][NH2:27])=[CH:24][CH:23]=2)[CH2:18][CH2:17]1.C1(C=CC(O)=CC=1)O.O>C(O)CCC>[Cl:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[C:5]([O:11][CH3:12])=[CH:4][C:3]=1[CH2:13][CH2:14][NH:27][CH2:26][C:25]1[CH:24]=[CH:23][C:22]([N:19]2[CH2:18][CH2:17][N:16]([CH3:15])[CH2:21][CH2:20]2)=[CH:29][CH:28]=1

Participants

6

Reactant 4

HCID 785HydroquinoneHCID 962WaterHCID 2776493[4-(4-Methylpiperazin-1-yl)phenyl]methanamineHCID 674659471-Chloro-4-methoxy-5-nitro-2-vinylbenzene

Product 1

HCID 674659782-(2-chloro-5-methoxy-4-nitrophenyl)-N-(4-(4-methylpiperazin-1-yl)benzyl)ethanamineYield 43%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A mixture of 1-chloro-4-methoxy-5-nitro-2-vinylbenzene (0.42 g, 1.95 mmol), 4-(4-methyl-piperazin-1-yl)-benzylamine (1.2 g, 5.85 mmol) and quinol (0.043 g, 0.39 mmol) in n-butanol (8 mL) was heated to reflux for 12 hours under a N2 atmosphere. Water (100 mL) was added and the reaction mixture extracted with EtOAc (3×100 mL). The combined organic extracts were washed with brine (50 mL), dried (Na2SO4) and concentrated under reduced pressure. The residue was purified by column chromatography on neutral silica gel using 3-5% methanol in DCM to give the title compound (0.35 g, 43%) as a solid.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 12 hours under a N2 atmosphere
  3. extractionthe reaction mixture extracted with EtOAc (3×100 mL)
  4. washThe combined organic extracts were washed with brine (50 mL)
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by column chromatography on neutral silica gel using 3-5% methanol in DCM

Sources & evidence

ORD record
ord-5e344b53b38647c18371b876261e3489
Source dataset
uspto-grants-2014_05
Patent number
US08716287B2

Reaction notes

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