HCID 59332343, compound → tert-Butyl 4-(3-aminopyridin-4-yl)piperazine-1-carboxylate

HRID 1879826Notes

Reaction equation

HRID 1879826 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][N:17]=[CH:16][C:15]=2[N+:20]([O-])=O)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>CO.CCOC(C)=O.[Pd]>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][N:11]([C:14]2[CH:19]=[CH:18][N:17]=[CH:16][C:15]=2[NH2:20])[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 59332343HCID 59332343, compound

Product 1

HCID 43462405tert-Butyl 4-(3-aminopyridin-4-yl)piperazine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21584119Ethylacetate methanolSolvent

Procedure

The 4-(3-nitro-pyridin-4-yl)-piperazine-1-carboxylic acid tert-butyl ester (633 mg) was then diluted with MeOH/EtOAc (1:1, 10 mL) and to the resulting solution was added Pd on carbon (5% Pd). The resulting reaction mixture was stirred under a hydrogen atmosphere at room temperature for about 15 hours. The reaction mixture was filtered through a pad of celite and the filtrate was concentrated in vacuo to provide 4-(3-amino-pyridin-4-yl)-piperazine-1-carboxylic acid tert-butyl ester as a solid form. HPLC-MS RT=1.10 min, mass calculated for formula C14H22N4O2 278.17, observed LCMS m/z 279.28 (M+H).

Workup

  1. customThe resulting reaction mixture
  2. filtrationThe reaction mixture was filtered through a pad of celite
  3. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-b7c8822e214f4c60967948f2989b740b
Source dataset
uspto-grants-2012_11
Patent number
US08318735B2

Reaction notes

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