Ammonium Chloride → 4-(4-tert-Butylpiperazin-1-yl)aniline

HRID 875145Notes

Reaction equation

HRID 875145 reaction equation
[C:1]([N:5]1[CH2:10][CH2:9][N:8]([C:11]2[CH:16]=[CH:15][C:14]([N+:17]([O-])=O)=[CH:13][CH:12]=2)[CH2:7][CH2:6]1)([CH3:4])([CH3:3])[CH3:2].[Cl-].[NH4+]>CO.O.[Fe]>[C:1]([N:5]1[CH2:10][CH2:9][N:8]([C:11]2[CH:12]=[CH:13][C:14]([NH2:17])=[CH:15][CH:16]=2)[CH2:7][CH2:6]1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 574441581-Tert-butyl-4-(4-nitrophenyl)piperazine

Product 1

HCID 242791824-(4-tert-Butylpiperazin-1-yl)anilineYield 89.6%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of 840 mg (3.189 mmol) of 1-tert-butyl-4-(4-nitrophenyl)piperazine in 24 mL of methanol, 904 mg (16.9 mmol) of ammonium chloride dissolved in 6 mL of water and 552 mg (9.886 mmol) of iron were added. After 7 hours, the suspension was cooled and filtered. pH was adjusted to 10 through portionwise addition of Na2CO3 to the aqueous phase. Extraction with dichloromethane yielded 667 mg of the title amine.

Workup

  1. temperaturethe suspension was cooled
  2. filtrationfiltered
  3. additionpH was adjusted to 10 through portionwise addition of Na2CO3 to the aqueous phase
  4. extractionExtraction with dichloromethane

Sources & evidence

ORD record
ord-a65a4aefd29a4937868104240a79cb80
Source dataset
uspto-grants-2015_03
Patent number
US08981089B2

Reaction notes

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