2-Nitro-5-piperidin-1-yl-benzoic acid ethyl ester → 2-Amino-5-piperidin-1-yl-benzoic acid ethyl ester

HRID 1094988Notes

Reaction equation

HRID 1094988 reaction equation
[CH2:1]([O:3][C:4](=[O:20])[C:5]1[CH:10]=[C:9]([N:11]2[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]2)[CH:8]=[CH:7][C:6]=1[N+:17]([O-])=O)[CH3:2].[H][H]>CO.[Pt]=O>[CH2:1]([O:3][C:4](=[O:20])[C:5]1[CH:10]=[C:9]([N:11]2[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]2)[CH:8]=[CH:7][C:6]=1[NH2:17])[CH3:2]

Participants

5

Reactant 2

HCID 666389632-Nitro-5-piperidin-1-yl-benzoic acid ethyl esterHCID 178418361HCID 178418361, compound

Product 1

HCID 613065672-Amino-5-piperidin-1-yl-benzoic acid ethyl ester

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 887MethanolSolvent

Procedure

Subsequently, crude 2-nitro-5-piperidin-1-yl-benzoic acid ethyl ester (3.8 g) was dissolved in methanol (35 ml), and platinum oxide (300 mg) was added to the solution at room temperature. The air in the reaction system was replaced by hydrogen, and the mixture was then stirred for 12 hr. After the completion of the reaction, the atmosphere in the reaction system was replaced by nitrogen, and the reaction solution was then filtered through Celite to remove platinum oxide, and was then concentrated under the reduced pressure to give crude 2-amino-5-piperidin-1-yl-benzoic acid ethyl ester (compound A) as a useful intermediate (3.4 g, crude yield 100%).

Workup

  1. customAfter the completion of the reaction
  2. filtrationthe reaction solution was then filtered through Celite
  3. customto remove platinum oxide
  4. concentrationwas then concentrated under the reduced pressure

Sources & evidence

ORD record
ord-67cc1112fd4f4c8e9bd791a2a0be7b7d
Source dataset
uspto-grants-2012_03
Patent number
US08134015B2

Reaction notes

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