Ethanol → 1,1-Dimethylethyl 4-(4-amino-3-methylphenyl)-1-piperazinecarboxylate

HRID 1267929Notes

Reaction equation

HRID 1267929 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][C:17]([N+:20]([O-])=O)=[C:16]([CH3:23])[CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Cl-].[NH4+].C(O)C>[Fe].O>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][C:17]([NH2:20])=[C:16]([CH3:23])[CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 702EthanolHCID 25517Ammonium ChlorideHCID 53763997Tert-butyl 4-(3-methyl-4-nitrophenyl)piperazine-1-carboxylate

Product 1

HCID 445223981,1-Dimethylethyl 4-(4-amino-3-methylphenyl)-1-piperazinecarboxylateYield 66.2%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 962WaterSolvent

Procedure

4-(3-Methyl-4-nitrophenyl)-piperazine-1-carboxylic acid tert-butyl ester (2 g), iron powder (1.74 g), ammonium chloride (1.67 g), ethanol (50 ml) and water (50 ml) were refluxed together under nitrogen for 2 hours. The mixture was cooled and the iron was filtered off. Water (200 ml) was added to the residue and the product extracted into ethyl acetate (3×200 ml), dried (MgSO4), and concentrated to give the sub-title compound (1.20 g).

Workup

  1. temperatureThe mixture was cooled
  2. filtrationthe iron was filtered off
  3. additionWater (200 ml) was added to the residue
  4. extractionthe product extracted into ethyl acetate (3×200 ml)
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-651db0607a204d1c8f7e7c95a50fffe3
Source dataset
uspto-grants-2003_04
Patent number
US06555541B1

Reaction notes

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