Tert-butyl 4-(4-nitrobenzoyl)piperazine-1-carboxylate → Tert-butyl 4-(4-aminobenzoyl)piperazine-1-carboxylate

HRID 2410711Notes

Reaction equation

HRID 2410711 reaction equation
[N+:1]([C:4]1[CH:24]=[CH:23][C:7]([C:8]([N:10]2[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12][CH2:11]2)=[O:9])=[CH:6][CH:5]=1)([O-])=O>CO.[Pd]>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([C:8]([N:10]2[CH2:11][CH2:12][N:13]([C:16]([O:18][C:19]([CH3:20])([CH3:22])[CH3:21])=[O:17])[CH2:14][CH2:15]2)=[O:9])=[CH:23][CH:24]=1

Participants

4

Reactant 1

HCID 2764459Tert-butyl 4-(4-nitrobenzoyl)piperazine-1-carboxylate

Product 1

HCID 2763355Tert-butyl 4-(4-aminobenzoyl)piperazine-1-carboxylateYield 99.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

tert-Butyl 4-(4-nitrobenzoyl)piperazine-1-carboxylate (12.9 g, 38.5 mmol) was dissolved in methanol (150 ml) and transferred into a 500-ml PARR flask. The flask was flushed with nitrogen, 10% Pd/C (0.38 g, 0.357 mmol) was added, flushed again with nitrogen, then hydrogen, then hydrogenate for 17 hours while shaking. (H2 pressure 50 psi). The reaction mixture was filtered through CELITE®, the CELITE® washed with MeOH and the collected liquids concentrated in vacuum. 11.67 g of tert-butyl 4-(4-amino-benzoyl)piperazine-1-carboxylate were isolated as a beige solid. MS (ESI) m/z 306 (M+H). 1H NMR (CDCl3) δ ppm 7.25 (d, 2H, J=7.7), 6.64 (d, 2H, J=7.7), 3.89 (bs, 2H), 3.58 (bs, 4H), 4.43 (bs, 4H), 1.46 (s, 9H).

Workup

  1. additionwas added
  2. customflushed again with nitrogen
  3. filtrationThe reaction mixture was filtered through CELITE®
  4. washthe CELITE® washed with MeOH
  5. concentrationthe collected liquids concentrated in vacuum

Sources & evidence

ORD record
ord-e81c4f760cbf41ad87403548372d6ee4
Source dataset
uspto-grants-2014_08
Patent number
US08815840B2

Reaction notes

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