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

HRID 714987Notes

Reaction equation

HRID 714987 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.[H][H]>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

5

Reactant 2

HCID 2764459tert-Butyl 4-(4-nitrobenzoyl)piperazine-1-carboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 2763355Tert-butyl 4-(4-aminobenzoyl)piperazine-1-carboxylateYield 93%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of tert-butyl 4-(4-nitrobenzoyl)piperazine-1-carboxylate (1.00 g, 3.00 mmol) in MeOH (60 ml) was hydrogenated at 20° C. at atmospheric pressure using an H-Cube (flow rate at 1 ml/min and full hydrogen mode) using a Pd/C cartridge. The solvent was removed in vacuo to afford tert-butyl 4-(4-aminobenzoyl)piperazine-1-carboxylate (0.85 g, 2.79 mmol, 93%) as a white solid. 1H NMR (CDCl3) δ 1.41 (9H, s), 3.38 (4H, m), 3.53 (4H, m), 4.07 (2H, br. s), 6.55 (2H, d), 7.17 (2H, d). LCMS (2) Rt: 2.14 min; m/z (ES+) 306.

Workup

  1. customwas hydrogenated at 20° C. at atmospheric pressure
  2. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-3c6f9c3a84b84b309d521ef70fa5f65d
Source dataset
uspto-grants-2015_11
Patent number
US09187465B2

Reaction notes

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