N-methyl-1-(1-benzyloxycarbonylpiperidin-4-yl)-1H-indole-6-carboxamide → 1-(piperidin-4-yl)-N-methyl-1H-indole-6-carboxamide

HRID 494915Notes

Reaction equation

HRID 494915 reaction equation
[CH3:1][NH:2][C:3]([C:5]1[CH:13]=[C:12]2[C:8]([CH:9]=[CH:10][N:11]2[CH:14]2[CH2:19][CH2:18][N:17](C(OCC3C=CC=CC=3)=O)[CH2:16][CH2:15]2)=[CH:7][CH:6]=1)=[O:4].[H][H]>CO.[C].[Pd]>[CH3:1][NH:2][C:3]([C:5]1[CH:13]=[C:12]2[C:8]([CH:9]=[CH:10][N:11]2[CH:14]2[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]2)=[CH:7][CH:6]=1)=[O:4]

Participants

5

Reactant 2

HCID 57682860N-methyl-1-(1-benzyloxycarbonylpiperidin-4-yl)-1H-indole-6-carboxamideHCID 178418361HCID 178418361, compound

Product 1

HCID 576828371-(piperidin-4-yl)-N-methyl-1H-indole-6-carboxamideYield 83.6%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalyst2×HCID 887MethanolSolvent

Procedure

1.77 g of N-methyl-1-(1-benzyloxycarbonylpiperidin-4-yl)-1H-indole-6-carboxamide was dissolved in 30 ml of methanol. Then, 200 mg of 10% palladium carbon was added to the obtained solution. The reaction atmosphere was replaced by hydrogen, and it was then stirred at room temperature. After completion of the reaction, 10% palladium carbon was filtered off from the reaction solution, and the reaction solution was then concentrated under a reduced pressure. The residue was purified by NH silica gel column chromatography (ethyl acetate/methanol), followed by solidification from a mixed solution consisting of ethyl acetate, t-butylmethyl ether, and methanol, so as to obtain 973 mg of the subject compound.

Workup

  1. customThe reaction atmosphere
  2. filtrationwas filtered off from the reaction solution
  3. concentrationthe reaction solution was then concentrated under a reduced pressure
  4. customThe residue was purified by NH silica gel column chromatography (ethyl acetate/methanol)

Sources & evidence

ORD record
ord-300aff1a8c3347148e59f89c6d1fa17c
Source dataset
uspto-grants-2009_05
Patent number
US07538123B2

Reaction notes

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