HCID 66711722, compound → HCID 66712498, compound

HRID 1262417Notes

Reaction equation

HRID 1262417 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH:9]1[C:21]1[CH:26]=[CH:25][C:24]([N+:27]([O-])=O)=[CH:23][CH:22]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>CO.[Pt]>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH:9]1[C:21]1[CH:26]=[CH:25][C:24]([NH2:27])=[CH:23][CH:22]=1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 1

HCID 66711722HCID 66711722, compound

Product 1

HCID 66712498HCID 66712498, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 887MethanolSolvent

Procedure

2-(4-Nitro-phenyl)-piperazine-1,4-dicarboxylic acid di-tert-butyl ester (0.440 g, 1.08 mmol) was dissolved in Methanol (40 mL) and transferred to a Parr bottle containing 5% Platinum on Carbon, Sulfided (0.5%) (65 mg, 0.017 mmol). The mixture was shaken under an atmosphere of Hydrogen (10 psi) for 2 h, then filtered and conc. in vacuo to afford 2-(4-Amino-phenyl)-piperazine-1,4-dicarboxylic acid di-tert-butyl ester (0.37 g, 91%). 1H-NMR (DMSO-d6): 6.88 (d, 2H, J=8.0 Hz), 6.51 (d, 2H, J=8.0 Hz), 5.00 (m, 3H), 4.26 (m, 1H), 3.77 (m, 2H), 3.16 (m, 1H), 2.84 (m, 2H), 1.39 (s, 9H), 1.35 (s, 9H).

Workup

  1. filtrationfiltered and conc. in vacuo

Sources & evidence

ORD record
ord-5e7f6d1b10ee492ba4ef83d745cc4543
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

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