Sodium Bicarbonate → tert-Butyl 4-((4-aminophenyl)methyl)piperazine-1-carboxylate

HRID 499198Notes

Reaction equation

HRID 499198 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([N+:21]([O-])=O)=[CH:17][CH:16]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].O.O.[Sn](Cl)(Cl)(Cl)Cl.C(=O)(O)[O-].[Na+]>C(OCC)(=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][N:11]([CH2:14][C:15]2[CH:16]=[CH:17][C:18]([NH2:21])=[CH:19][CH:20]=2)[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 235069461-Boc-4-(4-Nitrobenzyl)piperazineHCID 85782573Tin tetrachloride dihydrate

Product 1

HCID 12045001tert-Butyl 4-((4-aminophenyl)methyl)piperazine-1-carboxylateYield 89%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

4-(4-Nitro-benzyl)-piperazin-1-yl carboxylic acid tert-butyl ester (769 mg, 2.4 mmol) and tin chloride dihydrate (2.70 g, 12 mmol) are suspended in ethyl acetate (20 mL) and stirred at room temperature overnight. Then, saturated aqueous solution of sodium bicarbonate (20 mL) is added and vigorously stirred for 1 hour. Solids are removed by filtration and the organic layer of the filtrate is separated and washed with water (20 mL). The organic phase is dried over anhydrous magnesium sulfate and concentrated to give a white solid (620 mg, 89% yield, ES+(m/z) 293 [M+H]).

Workup

  1. stirringvigorously stirred for 1 hour
  2. customSolids are removed by filtration
  3. customthe organic layer of the filtrate is separated
  4. washwashed with water (20 mL)
  5. dry with materialThe organic phase is dried over anhydrous magnesium sulfate
  6. concentrationconcentrated
  7. customto give a white solid (620 mg, 89% yield, ES+(m/z) 293 [M+H])

Sources & evidence

ORD record
ord-22a6201100424ded8c68ca25f011162c
Source dataset
uspto-grants-2010_08
Patent number
US07767674B2

Reaction notes

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