2-[1-(1-Methoxycarbonylpiperidin-4-yl)-piperidin-4-yl]amino-3-nitropyridine → 3-Amino-2-[1-(1-methoxycarbonylpiperidin-4-yl)-piperidin-4-yl]aminopyridin

HRID 47533Notes

Reaction equation

HRID 47533 reaction equation
[CH3:1][O:2][C:3]([N:5]1[CH2:10][CH2:9][CH:8]([N:11]2[CH2:16][CH2:15][CH:14]([NH:17][C:18]3[C:23]([N+:24]([O-])=O)=[CH:22][CH:21]=[CH:20][N:19]=3)[CH2:13][CH2:12]2)[CH2:7][CH2:6]1)=[O:4].[H][H]>CO.[Pd]>[NH2:24][C:23]1[C:18]([NH:17][CH:14]2[CH2:15][CH2:16][N:11]([CH:8]3[CH2:9][CH2:10][N:5]([C:3]([O:2][CH3:1])=[O:4])[CH2:6][CH2:7]3)[CH2:12][CH2:13]2)=[N:19][CH:20]=[CH:21][CH:22]=1

Participants

5

Reactant 2

HCID 178310772-[1-(1-Methoxycarbonylpiperidin-4-yl)-piperidin-4-yl]amino-3-nitropyridineHCID 178418361HCID 178418361, compound

Product 1

HCID 227452603-Amino-2-[1-(1-methoxycarbonylpiperidin-4-yl)-piperidin-4-yl]aminopyridin

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Seventy (70) mg of 2-[1-(1-methoxycarbonylpiperidin-4-yl)-piperidin-4-yl]amino-3-nitropyridine was dissolved in 5 ml of methanol, and to which 20 mg of 10% palladium/carbon catalyst was added to effect catalytic reduction at room temperature under atmospheric pressure of hydrogen. After filtering the catalyst off and drying the filtrate to solid, the resulting residue was purified by silica gel column chromatography (chloroform/methanol=95/5) to give 20 mg of 3-amino-2-[1-(1-methoxycarbonylpiperidin-4-yl)-piperidin-4-yl]aminopyridin.

Workup

  1. customat room temperature
  2. filtrationAfter filtering the catalyst off and
  3. customdrying the filtrate to solid
  4. customthe resulting residue was purified by silica gel column chromatography (chloroform/methanol=95/5)

Sources & evidence

ORD record
ord-3c753ad01d3a4689adf159fe655e9a2f
Source dataset
uspto-grants-2004_03
Patent number
US06699880B1

Reaction notes

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