Ammonium Chloride → 3-{1-Methyl-2-[4-(2-methyl-5-quinolinyl)-1-piperazinyl]ethyl}aniline

HRID 734567Notes

Reaction equation

HRID 734567 reaction equation
[CH3:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][C:8]=2[N:12]2[CH2:17][CH2:16][N:15]([CH2:18][CH:19]([C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([N+:27]([O-])=O)[CH:22]=3)[CH3:20])[CH2:14][CH2:13]2)[N:3]=1.[Cl-].[NH4+]>CO.O.[Fe]>[CH3:20][CH:19]([C:21]1[CH:22]=[C:23]([CH:24]=[CH:25][CH:26]=1)[NH2:27])[CH2:18][N:15]1[CH2:14][CH2:13][N:12]([C:8]2[CH:7]=[CH:6][CH:5]=[C:4]3[C:9]=2[CH:10]=[CH:11][C:2]([CH3:1])=[N:3]3)[CH2:17][CH2:16]1

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 574443342-Methyl-5-{4-[2-(3-nitrophenyl)propyl]-1-piperazinyl}quinoline

Product 1

HCID 574443353-{1-Methyl-2-[4-(2-methyl-5-quinolinyl)-1-piperazinyl]ethyl}anilineYield 61.9%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of 2-methyl-5-{4-[2-(3-nitrophenyl)propyl]-1-piperazinyl}quinoline (70 mg) in methanol (1 mL) was added dropwise to a stirred suspension of iron powder (3.0 equiv., 30 mg) and ammonium chloride (5.0 equiv., 48 mg) in water (1 mL). The reactants were heated at reflux for 18 hours. The reaction mixture was cooled to room temperature then filtered using a Millipore filter. The filtrate was concentrated under reduced pressure and purified using chromatography (SiO2, SPE) eluting with DCM-methanol (95:5) to afford the title compound (40 mg, 60% yield).

Workup

  1. temperatureThe reactants were heated
  2. temperatureat reflux for 18 hours
  3. filtrationthen filtered
  4. filtrationfilter
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. custompurified
  7. washeluting with DCM-methanol (95:5)

Sources & evidence

ORD record
ord-a801906fea21425c8a08029c3bbe5b9d
Source dataset
uspto-grants-2009_09
Patent number
US07592346B2

Reaction notes

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