Sodium Bicarbonate → Tert-Butyl 4-(4-Amino-2-Chlorophenyl)Piperazine-1-Carboxylate

HRID 1503833Notes

Reaction equation

HRID 1503833 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([N+:8]([O-])=O)[CH:5]=[CH:4][C:3]=1[N:11]1[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH2:12]1.O1CCCC1.CO.C(=O)([O-])O.[Na+]>[Zn].C(O)(=O)C>[NH2:8][C:6]1[CH:5]=[CH:4][C:3]([N:11]2[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:22])([CH3:21])[CH3:23])=[O:18])[CH2:13][CH2:12]2)=[C:2]([Cl:1])[CH:7]=1

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 18783805Tert-butyl 4-(2-chloro-4-nitrophenyl)piperazine-1-carboxylateHCID 21899815MeOH tetrahydrofuran

Product 1

HCID 18783766Tert-Butyl 4-(4-Amino-2-Chlorophenyl)Piperazine-1-Carboxylate

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

To a solution of the product of Example 18A (1.5 g, 4.4 mmol) in 1:1 tetrahydrofuran/methanol (80 mL) at ambient temperature was slowly added zinc power (1.43 g, 22 mmol) and acetic acid (5 mL). The mixture was stirred for 1 hour, and saturated aqueous sodium hydrogen carbonate solution was added. The mixture was stirred for 1 hour and filtered, and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate, filtered, and concentrated. The residue was purified by flash chromatography on silica gel eluting with 5/1 petroleum ether/ethyl acetate to give title compound. MS: 312 (M+H+).

Workup

  1. customat ambient temperature
  2. stirringThe mixture was stirred for 1 hour
  3. filtrationfiltered
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was purified by flash chromatography on silica gel eluting with 5/1 petroleum ether/ethyl acetate

Sources & evidence

ORD record
ord-87eb4341f5dd46bf9f8137cf8654aa52
Source dataset
uspto-grants-2015_12
Patent number
US09212192B2

Reaction notes

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