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

HRID 1924987Notes

Reaction equation

HRID 1924987 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-0ac1251a0c984d6dad5fe61c224cb312
Source dataset
uspto-grants-2012_05
Patent number
US08178530B2

Reaction notes

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