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

HRID 2298074Notes

Reaction equation

HRID 2298074 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 67.3%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 962WaterSolvent

Procedure

4-(3-Methyl-4-nitrophenyl)piperazine-1-carboxylic acid tert-butyl ester (2 g, Example 36a), iron powder (1.74 g), ammonium chloride (1.67 g), ethanol (50 ml) and water (50 ml) were refluxed together under nitrogen for 2 h. 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 subtitle compound (1.22 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-386f0bac13b94dabbd810a8af75abd5b
Source dataset
uspto-grants-2002_12
Patent number
US06492355B1

Reaction notes

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