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

HRID 44640Notes

Reaction equation

HRID 44640 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-e7e685d6fe9e494f97c7dc5fcc2eda18
Source dataset
uspto-grants-2013_09
Patent number
US08541429B2

Reaction notes

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