Methanol → 4-((4-Methylpiperazin-1-yl)methyl)aniline

HRID 1947207Notes

Reaction equation

HRID 1947207 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([CH2:8][C:9]2[CH:14]=[CH:13][C:12]([N+:15]([O-])=O)=[CH:11][CH:10]=2)[CH2:4][CH2:3]1.CO.[Cl-].[NH4+]>[Zn].C(OCC)C>[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([CH2:8][C:9]2[CH:14]=[CH:13][C:12]([NH2:15])=[CH:11][CH:10]=2)[CH2:4][CH2:3]1

Participants

6

Reactant 3

HCID 887MethanolHCID 25517Ammonium ChlorideHCID 6777951-Methyl-4-(4-nitrobenzyl)piperazine

Product 1

HCID 31539964-((4-Methylpiperazin-1-yl)methyl)anilineYield 77.3%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 3283Diethyl EtherSolvent

Procedure

1-methyl-4-(4-nitrobenzyl)-piperazine (F652-01, 4.67 g, 19.9 mmol), methanol (100 mL), zinc powder (6.5 g, 99.3 mmol) and ammonium chloride (4.3 g, 79.5 mmol) were placed in a reaction vessel and heated for 2 hours under reflux. After returning to room temperature, the reaction mixture was filtered through Celite. The solvent of the filtrate was distilled off under reduced pressure to obtain a solid. Diethyl ether was added to the solid, and insoluble components were removed by filtration. 4-(4-methylpiperazin-1-ylmethyl)phenylamine (F652-02, white solid, 3.16 g, 77%) was obtained by removing the solvent of the filtrate by distillation.

Workup

  1. temperatureheated for 2 hours
  2. temperatureunder reflux
  3. customAfter returning to room temperature
  4. filtrationthe reaction mixture was filtered through Celite
  5. distillationThe solvent of the filtrate was distilled off under reduced pressure
  6. customto obtain a solid
  7. customwere removed by filtration

Sources & evidence

ORD record
ord-7212c0d3a057432281b24629c4ff54b6
Source dataset
uspto-grants-2013_03
Patent number
US08399464B2

Reaction notes

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