Hydroquinone → Tert-butyl 4-(4-((2-chloro-5-methoxy-4-nitrophenethylamino)methyl)phenyl)piperazine-1-carboxylate

HRID 1019779Notes

Reaction equation

HRID 1019779 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][C:17]([CH2:20][NH2:21])=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Cl:22][C:23]1[CH:28]=[C:27]([N+:29]([O-:31])=[O:30])[C:26]([O:32][CH3:33])=[CH:25][C:24]=1[CH:34]=[CH2:35].C1(C=CC(O)=CC=1)O>C(O)(C)C>[Cl:22][C:23]1[CH:28]=[C:27]([N+:29]([O-:31])=[O:30])[C:26]([O:32][CH3:33])=[CH:25][C:24]=1[CH2:34][CH2:35][NH:21][CH2:20][C:17]1[CH:16]=[CH:15][C:14]([N:11]2[CH2:10][CH2:9][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[CH2:13][CH2:12]2)=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 785HydroquinoneHCID 27638411,1-Dimethylethyl 4-[4-(aminomethyl)phenyl]-1-piperazinecarboxylateHCID 674659471-Chloro-4-methoxy-5-nitro-2-vinylbenzene

Product 1

HCID 67467855Tert-butyl 4-(4-((2-chloro-5-methoxy-4-nitrophenethylamino)methyl)phenyl)piperazine-1-carboxylateYield 65.1%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A stirred solution of 4-(4-aminomethyl-phenyl)-piperazine-1-carboxylic acid tert-butyl ester (0.531 g, 1.82 mmol), 1-chloro-4-methoxy-5-nitro-2-vinylbenzene (Example 50C) (0.3 g, 1.40 mmol) and quinol (61.8 mg, 0.562 mmol) in isopropyl alcohol (16 mL) was heated to 100° C. for 30 hours. The mixture was allowed to cool to room temperature and concentrated under reduced pressure. The residue was purified by column chromatography on neutral silica gel using 2% methanol in DCM to give the title compound (0.460 g, 65%)

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe residue was purified by column chromatography on neutral silica gel using 2% methanol in DCM

Sources & evidence

ORD record
ord-02dbb664e655438a818edb5e3956a70e
Source dataset
uspto-grants-2014_05
Patent number
US08716287B2

Reaction notes

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