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

HRID 1366203Notes

Reaction equation

HRID 1366203 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

1-Isopropyl-4-(4-nitro-phenyl)-piperazine (8.3 g, 33.2 mmol) is dissolved in MeOH (120 mL) and tin (II) dichloride dihydrate (37.4 g, 0.165 mol) is added. 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 (3×) and the organic layers combined, dried over MgSO4, filtered, concentrated in vacuo 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 (3×)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f11231af30f64f048fb05a33a62a79b2
Source dataset
uspto-grants-2011_02
Patent number
US07893058B2

Reaction notes

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