HCID 86708645, compound → HCID 86708644, compound

HRID 921762Notes

Reaction equation

HRID 921762 reaction equation
[Cl:1][C:2]1[C:7]([N+:8]([O-])=O)=[CH:6][C:5]([NH:11][C:12](=[O:15])[O:13][CH3:14])=[CH:4][C:3]=1[C:16]1[CH2:17][CH2:18][N:19]([CH3:22])[CH2:20][CH:21]=1>CO.C(OCC)(=O)C.[Pt](=O)=O>[NH2:8][C:7]1[CH:6]=[C:5]([NH:11][C:12](=[O:15])[O:13][CH3:14])[CH:4]=[C:3]([CH:16]2[CH2:17][CH2:18][N:19]([CH3:22])[CH2:20][CH2:21]2)[C:2]=1[Cl:1]

Participants

5

Reactant 1

HCID 86708645HCID 86708645, compound

Product 1

HCID 86708644HCID 86708644, compoundYield 67.3%

Reagents, catalysts & solvents 3

HCID 345198Adams' catalystCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of methyl (4-chloro-3-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-5-nitrophenyl)carbamate (213 mg, 0.654 mmol) and platinum (IV) oxide (240 mg, 0.654 mmol) in a mixture of MeOH (50 mL) and ethyl acetate (3 mL) was hydrogenated (balloon of H2). The reaction completed within 1 h. The catalyst was removed by filtration through a celite pad and the pad was rinsed with MeOH. The solvent was removed and radial silica gel chromatography, eluting with DCM containing 0 to 3% MeOH gave methyl (3-amino-4-chloro-5-(1-methylpiperidin-4-yl)phenyl)carbamate (131 mg) as a white solid.

Workup

  1. customThe catalyst was removed by filtration through a celite pad
  2. washthe pad was rinsed with MeOH
  3. customThe solvent was removed
  4. washradial silica gel chromatography, eluting with DCM containing 0 to 3% MeOH

Sources & evidence

ORD record
ord-fff771888b164f6cb7830f1222c81b72
Source dataset
uspto-grants-2016_03
Patent number
US09273057B2

Reaction notes

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