Ethyl Acetate → 4-(3-Amino-5-chloro-pyridin-2-yl)-piperazine-1-carboxylic acid tert-butyl ester

HRID 1810966Notes

Reaction equation

HRID 1810966 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[C:19]([N+:20]([O-])=O)=[CH:18][C:17]([Cl:23])=[CH:16][N:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(OCC)(=O)C>[Pt]=S.CO>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][N:11]([C:14]2[C:19]([NH2:20])=[CH:18][C:17]([Cl:23])=[CH:16][N:15]=2)[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 8857Ethyl AcetateHCID 595487524-(5-Chloro-3-nitro-pyridin-2-yl)-piperazine-1-carboxylic acid tert-butyl ester

Product 1

HCID 595488674-(3-Amino-5-chloro-pyridin-2-yl)-piperazine-1-carboxylic acid tert-butyl esterYield 80%

Reagents, catalysts & solvents 2

HCID 82861Platinum sulfide (PtS)CatalystHCID 887MethanolSolvent

Procedure

A round bottom flask is charged with 5% platinum sulfide on carbon (0.20 g, 0.039 mmol). The flask was evacuated and refilled with argon three times. To the flask is added 4-(5-chloro-3-nitro-pyridin-2-yl)-piperazine-1-carboxylic acid tert-butyl ester (2.80 g, 8.17 mmol) as a solution in a 1:1 mixture of ethyl acetate:methanol (100 mL). The mixture is placed under an atmosphere of hydrogen and stirred overnight at room temperature. The mixture is filtered through a pad of diatomaceous earth and concentrated under reduced pressure to provide 2.0 g of 4-(3-amino-5-chloro-pyridin-2-yl)-piperazine-1-carboxylic acid tert-butyl ester as a dark solid in 80% yield.

Workup

  1. customThe flask was evacuated
  2. additionrefilled with argon three times
  3. filtrationThe mixture is filtered through a pad of diatomaceous earth
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-8b8d07f68af74df58478088be04b392d
Source dataset
uspto-grants-2013_01
Patent number
US08362249B2

Reaction notes

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