Carbon Dioxide → 1-(4-Amino-phenyl)-piperidine-4-carboxylic acid methoxy-methyl-amide dihydrochloride

HRID 2236831Notes

Reaction equation

HRID 2236831 reaction equation
[CH3:1][O:2][N:3]([CH3:21])[C:4]([CH:6]1[CH2:11][CH2:10][N:9]([C:12]2[CH:17]=[CH:16][C:15]([N+:18]([O-])=O)=[CH:14][CH:13]=2)[CH2:8][CH2:7]1)=[O:5].C(=O)=O.[H][H].[ClH:27]>C(O)C.C(OCC)(=O)C.[Pd]>[ClH:27].[ClH:27].[CH3:1][O:2][N:3]([CH3:21])[C:4]([CH:6]1[CH2:11][CH2:10][N:9]([C:12]2[CH:13]=[CH:14][C:15]([NH2:18])=[CH:16][CH:17]=2)[CH2:8][CH2:7]1)=[O:5]

Participants

7

Reactant 4

HCID 280Carbon DioxideHCID 313Hydrochloric AcidHCID 86098660N-methoxy-N-methyl-1-(4-nitrophenyl)piperidine-4-carboxamideHCID 178418361HCID 178418361, compound

Product 1

HCID 875430171-(4-Amino-phenyl)-piperidine-4-carboxylic acid methoxy-methyl-amide dihydrochlorideYield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21584252Ethanol ethylacetateSolvent

Procedure

A solution of 1-(4-nitro-phenyl)-piperidine-4-carboxylic acid methoxy-methyl-amide (approximately 0.20 g, 0.8 mmol) in ethanol/ethyl acetate (1:1, 30 mL) and concentrated hydrochloric acid (1 mL) is degassed with dry ice. Palladium on carbon (10%, 35 mg) is added and the mixture is shaken for two hours under 40 psi of hydrogen. The mixture is filtered through a pad of diatomaceous earth and concentrated under reduced pressure to give 1-(4-amino-phenyl)-piperidine-4-carboxylic acid methoxy-methyl-amide dihydrochloride (0.30 g, >100%).

Workup

  1. filtrationThe mixture is filtered through a pad of diatomaceous earth
  2. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-38616f058d0d4baf82f163be2244a000
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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