Ammonium Chloride → (+/-)-tert-Butyl 3-methyl-4-(4-aminophenyl)piperazine-1-carboxylate

HRID 2416655Notes

Reaction equation

HRID 2416655 reaction equation
[CH3:1][CH:2]1[N:7]([C:8]2[CH:13]=[CH:12][C:11]([N+:14]([O-])=O)=[CH:10][CH:9]=2)[CH2:6][CH2:5][N:4]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:3]1.[Cl-].[NH4+]>C(O)C.[Fe]>[CH3:1][CH:2]1[N:7]([C:8]2[CH:9]=[CH:10][C:11]([NH2:14])=[CH:12][CH:13]=2)[CH2:6][CH2:5][N:4]([C:17]([O:19][C:20]([CH3:21])([CH3:23])[CH3:22])=[O:18])[CH2:3]1

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 22633044Tert-butyl 3-methyl-4-(4-nitrophenyl)piperazine-1-carboxylate

Product 1

HCID 22633057(+/-)-tert-Butyl 3-methyl-4-(4-aminophenyl)piperazine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Procedure

To a mixture of (±)-tert-butyl 3-methyl-4-(4-nitrophenyl)piperazine-1-carboxylate (870 mg) and iron powder (378 mg) in ethanol (16 ml) was added an aqueous solution (4 ml) of ammonium chloride (116 mg) at room temperature. The resulting suspension was refluxed for 2 hours with vigorous stirring. The reaction mixture was cooled to room temperature, and the resulting solid was filtered through celite and thoroughly washed with ethyl acetate. The filtrate was separated, and the aqueous layer was extracted with ethyl acetate twice. The organic layers were combined and washed successively with saturated aqueous sodium hydrogencarbonate solution and brine. The solvent was evaporated to give the title compound as a yellow oil.

Workup

  1. temperatureThe resulting suspension was refluxed for 2 hours with vigorous stirring
  2. filtrationthe resulting solid was filtered through celite and
  3. washthoroughly washed with ethyl acetate
  4. customThe filtrate was separated
  5. extractionthe aqueous layer was extracted with ethyl acetate twice
  6. washwashed successively with saturated aqueous sodium hydrogencarbonate solution and brine
  7. customThe solvent was evaporated

Sources & evidence

ORD record
ord-d5b07886addc43f198831d450d674e25
Source dataset
uspto-grants-2004_11
Patent number
US06825200B1

Reaction notes

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