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

HRID 1783967Notes

Reaction equation

HRID 1783967 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].O.O.[Sn](Cl)Cl.Cl>CO>[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

5

Reactant 3

HCID 313Hydrochloric AcidHCID 61436Stannous chloride dihydrateHCID 339957181-Isopropyl-4-(5-nitro-pyridin-2-yl)-piperazine

Product 1

HCID 434620426-(4-Isopropyl-piperazin-1-yl)-pyridin-3-yl-amineYield 86%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1-Isopropyl-4-(5-nitro-pyridin-2-yl)-piperazine (0.9 g, 3.6 mmol) is dissolved in MeOH (20 mL) and tin (II) dichloride dihydrate (4 g, 18 mmol) is added. The mixture is cooled using a water bath and conc. HCl is added (4 mL). The reaction is stirred at room temperature overnight. After removing the methanol, the resultant light yellow solution is basified using conc. NaOH (pH 11) and a white precipitate is formed. The solid is collected by filtration and the water is extracted with diethyl ether (5×). The organic layers are combined, dried over MgSO4, filtered, concentrated under vacuum to afford an orange oil which crystallizes on standing to afford an orange solid (0.68 g, 86%).

Workup

  1. temperatureThe mixture is cooled
  2. customAfter removing the methanol
  3. customa white precipitate is formed
  4. filtrationThe solid is collected by filtration
  5. extractionthe water is extracted with diethyl ether (5×)
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated under vacuum
  9. customto afford an orange oil which
  10. customcrystallizes

Sources & evidence

ORD record
ord-c30382f053ff4f0eb8c94e28cb95ba2f
Source dataset
uspto-grants-2009_03
Patent number
US07501411B2

Reaction notes

Loading…