Ethyl 3-nitro-4-(piperidin-1-yl)benzoate → Ethyl 3-amino-4-(1-piperidinyl)benzoate

HRID 1498894Notes

Reaction equation

HRID 1498894 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:12]=[CH:13][C:14]=1[N:15]1[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1)[C:7]([O:9][CH2:10][CH3:11])=[O:8])([O-])=O>CO.[Pd]>[NH2:1][C:4]1[CH:5]=[C:6]([CH:12]=[CH:13][C:14]=1[N:15]1[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1)[C:7]([O:9][CH2:10][CH3:11])=[O:8]

Participants

4

Reactant 1

HCID 12493642Ethyl 3-nitro-4-(piperidin-1-yl)benzoate

Product 1

HCID 2818633Ethyl 3-amino-4-(1-piperidinyl)benzoateYield 90%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Ethyl 3-nitro-4-piperidin-1-ylbenzoate (2.83 g, 10.2 mmol) prepared in the Step 3-1-1 was dissolved in methanol (50 ml), and palladium 5% on carbon (500 mg) was added to the solution. The mixture was stirred under a hydrogen flow at a room temperature overnight. The mixture was filtered, and the filtrate was concentrated to give the title compound (2.23 g, 90%) as a blackish-red solid.

Workup

  1. filtrationThe mixture was filtered
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-ede8156cfc33498e952fe071858ac280
Source dataset
uspto-grants-2015_12
Patent number
US09200008B2

Reaction notes

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