1-(3-Dimethylcarbamoyl-4-nitrophenyl)piperidine-4-carboxylic acid ethyl ester → 1-(4-Amino-3-dimethylcarbamoylphenyl)piperidine-4-carboxylic acid ethyl ester

HRID 423282Notes

Reaction equation

HRID 423282 reaction equation
[CH2:1]([O:3][C:4]([CH:6]1[CH2:11][CH2:10][N:9]([C:12]2[CH:17]=[CH:16][C:15]([N+:18]([O-])=O)=[C:14]([C:21](=[O:25])[N:22]([CH3:24])[CH3:23])[CH:13]=2)[CH2:8][CH2:7]1)=[O:5])[CH3:2]>O1CCCC1.C(O)C.[H][H].[C].[Pd]>[CH2:1]([O:3][C:4]([CH:6]1[CH2:11][CH2:10][N:9]([C:12]2[CH:17]=[CH:16][C:15]([NH2:18])=[C:14]([C:21](=[O:25])[N:22]([CH3:24])[CH3:23])[CH:13]=2)[CH2:8][CH2:7]1)=[O:5])[CH3:2]

Participants

6

Reactant 1

HCID 666765811-(3-Dimethylcarbamoyl-4-nitrophenyl)piperidine-4-carboxylic acid ethyl ester

Product 1

HCID 666769441-(4-Amino-3-dimethylcarbamoylphenyl)piperidine-4-carboxylic acid ethyl ester

Reagents, catalysts & solvents 4

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolventHCID 178418361HCID 178418361, compoundSolvent

Procedure

1-(3-Dimethylcarbamoyl-4-nitrophenyl)-piperidine-4-carboxylic acid ethyl ester (1.578 g) was dissolved in tetrahydrofuran (5 mL) and ethanol (5 mL). After addition of 7.5% (w/w) palladium-carbon (0.316 g) to the solution, the mixture was stirred for 5 hours at normal pressure in hydrogen atmosphere. The reaction solution was filtered through a Celite pad and concentrated to give the title compound, which was used without isolation in the subsequent reaction.

Workup

  1. filtrationThe reaction solution was filtered through a Celite pad
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-1ae13ef4120e42a890fbf0c6cbb8f7a6
Source dataset
uspto-grants-2012_01
Patent number
US08101774B2

Reaction notes

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