Hydrochloric Acid → 2-(Piperazin-1-yl)pyridin-3-amine

HRID 2209890Notes

Reaction equation

HRID 2209890 reaction equation
[N:1]1([C:7]2[C:12]([N+:13]([O-])=O)=[CH:11][CH:10]=[CH:9][N:8]=2)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.Cl>C(O)C>[NH2:13][C:12]1[C:7]([N:1]2[CH2:2][CH2:3][NH:4][CH2:5][CH2:6]2)=[N:8][CH:9]=[CH:10][CH:11]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 37788341-(3-Nitropyridin-2-yl)piperazine

Product 1

HCID 103973582-(Piperazin-1-yl)pyridin-3-amine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-(1-piperazinyl)-3-nitropyridine (24.50 g), ethanol (445 ml) and hydrochloric acid (1.2N, 44 ml) are combined and hydrogenated overnight at 40 psi, refilling when necessary. The mixture is filtered through celite, washed with ethanol, chloroform, ethanol and water. The organic solvents are removed with heat and reduced pressure. The remaining material is partitioned between methylene chloride (3×250 ml) and sodium bicarbonate. The organic layers are combined, dried over potassium carbonate, filtered and concentrated under reduced pressure to give an oil which slowly solidified upon standing to give 3-amino-2-(1-piperazinyl)pyridine.

Workup

  1. filtrationThe mixture is filtered through celite
  2. washwashed with ethanol, chloroform, ethanol and water
  3. customThe organic solvents are removed
  4. temperaturewith heat
  5. customThe remaining material is partitioned between methylene chloride (3×250 ml) and sodium bicarbonate
  6. dry with materialdried over potassium carbonate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customto give an oil which

Sources & evidence

ORD record
ord-d277773279ae400abb877744f4446fbf
Source dataset
uspto-grants-1995_10
Patent number
USRE035053

Reaction notes

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