Ammonia → 6-(4-Isopropyl-piperazin-1-yl)-pyridin-3-yl-amine

HRID 409695Notes

Reaction equation

HRID 409695 reaction equation
[CH:1]([N:4]1[CH2:9][CH2:8][N:7]([C:10]2[CH:15]=[CH:14][C:13]([N+:16]([O-])=O)=[CH:12][N:11]=2)[CH2:6][CH2:5]1)([CH3:3])[CH3:2].CCO.O.N>[Fe].CC(O)=O>[CH:1]([N:4]1[CH2:5][CH2:6][N:7]([C:10]2[N:11]=[CH:12][C:13]([NH2:16])=[CH:14][CH:15]=2)[CH2:8][CH2:9]1)([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 222AmmoniaHCID 702EthanolHCID 962WaterHCID 339957181-Isopropyl-4-(5-nitro-pyridin-2-yl)-piperazine

Product 1

HCID 434620426-(4-Isopropyl-piperazin-1-yl)-pyridin-3-yl-amine

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of iron powder (1.4 g, 25.3 mmol, 4 equiv), 1-isopropyl-4-(5-nitro-pyridin-2-yl)piperazine (1.58 g, 6.32 mmol), EtOH (20 mL), H2O (5 mL), and AcOH (2.5 mL) is stirred for 2 h at 90° C., allowed to cool to RT, basified by addition of aqueous ammonia, filtered through a pad of celite and partially concentrated to remove EtOH. The aqueous residue is saturated with sodium chloride and extracted with EtOAc and DCM. The combined organic phase is washed with brine, dried (Na2SO4), filtered and concentrated. The residue is purified by silica gel column chromatography (DCM/MeOH/NH3aq, 91:8:1) to afford the title compound as a purple solid: ESI-MS: 221.1 [MH]+; TLC: Rf=0.20 (DCM/MeOH/NH3aq, 91:8:1).

Workup

  1. temperatureto cool to RT
  2. filtrationfiltered through a pad of celite
  3. concentrationpartially concentrated
  4. customto remove EtOH
  5. extractionextracted with EtOAc and DCM
  6. washThe combined organic phase is washed with brine
  7. dry with materialdried (Na2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe residue is purified by silica gel column chromatography (DCM/MeOH/NH3aq, 91:8:1)

Sources & evidence

ORD record
ord-a1a900b102474e85bb00a0a23552f74b
Source dataset
uspto-grants-2014_06
Patent number
US08759517B2

Reaction notes

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