Ammonium Chloride → 5-(4-Methylpiperazin-1-yl)pyridin-2-amine

HRID 1918972Notes

Reaction equation

HRID 1918972 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:9]=[N:10][C:11]([N+:14]([O-])=O)=[CH:12][CH:13]=2)[CH2:4][CH2:3]1.[NH4+].[Cl-]>CCO.O.[Fe]>[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:13]=[CH:12][C:11]([NH2:14])=[N:10][CH:9]=2)[CH2:4][CH2:3]1

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 517114841-Methyl-4-(6-nitropyridin-3-yl)piperazine2×

Product 1

HCID 223298335-(4-Methylpiperazin-1-yl)pyridin-2-amineYield 60%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 19096565Water ethanolSolvent

Procedure

The suspension of 1-methyl-4-(6-nitropyridin-3-yl)piperazine (5 g, 22.5 mmol), NH4Cl (12 g, 225 mmol), and Fe (5 g, 5 mmol) was stirred in EtOH/H2O (1:1) (100 mL) at 80° C. for 3 h. TLC showed starting material 1-methyl-4-(6-nitropyridin-3-yl)piperazine disappeared. After filtration on a pad of Celite, the solvent was removed under vacuum. EA and brine were added into the mixture and the organic layer was separated, dried over Na2SO4 and concentrated at reduced pressure to give 2.5 g of 5-(4-methylpiperazin-1-yl)pyridin-2-amine (yield 60%). LCMS: (M+H)+ 193

Workup

  1. filtrationAfter filtration on a pad of Celite
  2. customthe solvent was removed under vacuum
  3. additionEA and brine were added into the mixture
  4. customthe organic layer was separated
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated at reduced pressure

Sources & evidence

ORD record
ord-5880db29c803426a8d08e62a73b5d696
Source dataset
uspto-grants-2013_12
Patent number
US08618107B2

Reaction notes

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