2-Methoxy-5-nitroaniline → 1-(2-methoxy-5-nitrophenyl)piperazine

HRID 859906Notes

Reaction equation

HRID 859906 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[CH:5][C:4]=1[NH2:12].Cl.Cl[CH2:15][CH2:16][NH:17][CH2:18][CH2:19]Cl.C(=O)([O-])[O-].[K+].[K+]>ClC1C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[CH:5][C:4]=1[N:12]1[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]1

Participants

5

Reactant 3

HCID 74472-Methoxy-5-nitroanilineHCID 11430Potassium CarbonateHCID 522769Bis(2-chloroethyl)amine hydrochloride

Product 1

HCID 37831381-(2-methoxy-5-nitrophenyl)piperazineYield 45.1%

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Procedure

A mixture of 2-methoxy-5-nitro-phenylamine (16.8 g, 0.1 mol), bis-(2-chloro-ethyl)-amine hydrochloride (17.8 g, 0.1 mol) and potassium carbonate (69 g, 0.5 mol) in chlorobenzene (300 ml) was refluxed for 48 h, washed by water. The water phase was extracted with dichloromethane. The organic layers were combined, dried over sodium sulfate, purified with flash chromatography on silica gel (CH2Cl2/MeOH) to give the desired product, 1-(2-methoxy-5-nitrophenyl)piperazine (10.7 g, 45%).

Workup

  1. temperaturewas refluxed for 48 h
  2. washwashed by water
  3. extractionThe water phase was extracted with dichloromethane
  4. dry with materialdried over sodium sulfate
  5. custompurified with flash chromatography on silica gel (CH2Cl2/MeOH)

Sources & evidence

ORD record
ord-bf47559bfe2a45a08a3640d3ab12772b
Source dataset
uspto-grants-2006_12
Patent number
US07153858B2

Reaction notes

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