Hydrochloric Acid → 4-[4-(Propan-2-yl)piperazin-1-yl]aniline

HRID 552386Notes

Reaction equation

HRID 552386 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][CH:11]=2)[CH2:6][CH2:5]1)([CH3:3])[CH3:2].O.O.[Sn](Cl)Cl.Cl>CO>[CH:1]([N:4]1[CH2:9][CH2:8][N:7]([C:10]2[CH:11]=[CH:12][C:13]([NH2:16])=[CH:14][CH:15]=2)[CH2:6][CH2:5]1)([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 61436Stannous chloride dihydrateHCID 98347891-Isopropyl-4-(4-nitrophenyl)piperazine

Product 1

HCID 91615454-[4-(Propan-2-yl)piperazin-1-yl]anilineYield 88%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 1-isopropyl-4-(4-nitro-phenyl)-piperazine (8.3 g, 33.2 mmol) in MeOH (120 mL) is added tin (II) dichloride dihydrate (37.4 g, 0.165 mol). The mixture is cooled using a water bath and conc. HCl is added (36 mL). The reaction is stirred at room temperature overnight. After removing the methanol, the resultant solution is basified using conc. NaOH (pH 11). The water phase is extracted with diethyl ether. The combined organic layer are dried (MgSO4), filtered and the solvent is removed under reduced pressure to afford the title compound (6.4 g, 88%).

Workup

  1. temperatureThe mixture is cooled
  2. customAfter removing the methanol
  3. extractionThe water phase is extracted with diethyl ether
  4. dry with materialThe combined organic layer are dried (MgSO4)
  5. filtrationfiltered
  6. customthe solvent is removed under reduced pressure

Sources & evidence

ORD record
ord-c1bf0d0faa8c4af49ac84635fdf70868
Source dataset
uspto-grants-2011_05
Patent number
US07951818B2

Reaction notes

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