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

HRID 1725554Notes

Reaction equation

HRID 1725554 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-bd125f31f09b4345910a67e34ca431b4
Source dataset
uspto-grants-2009_02
Patent number
US07491727B2

Reaction notes

Loading…