Benzoic acid, 3-nitro-4-(1-piperidinyl)-, methyl ester → methyl 3-amino-4-piperidin-1-ylbenzoate

HRID 406392Notes

Reaction equation

HRID 406392 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:11]=[CH:12][C:13]=1[N:14]1[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1)[C:7]([O:9][CH3:10])=[O:8])([O-])=O>CO.[C].[Pd]>[NH2:1][C:4]1[CH:5]=[C:6]([CH:11]=[CH:12][C:13]=1[N:14]1[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1)[C:7]([O:9][CH3:10])=[O:8]

Participants

4

Reactant 1

HCID 2878938Benzoic acid, 3-nitro-4-(1-piperidinyl)-, methyl ester

Product 1

HCID 1250441methyl 3-amino-4-piperidin-1-ylbenzoateYield 85.2%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

Using 10% palladium carbon cartridge, a solution of methyl 3-nitro-4-(piperidin-1-yl)benzoate (3.07 g) in methanol (50 ml) was pumped through the H-Cube™ reactor (ThalesNano Inc.). After all the reaction mixture had passed through the H-Cube™ reactor, the reaction mixture was concentrated under reduced pressure. The residue was purified by NH-silica gel column chromatography to obtain a title compound (2.32 g).

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. customThe residue was purified by NH-silica gel column chromatography

Sources & evidence

ORD record
ord-499299740561403c805c413cc3cb0f8b
Source dataset
uspto-grants-2014_06
Patent number
US08754100B2

Reaction notes

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