N-[2-(N-methyl-N-benzylamino)ethyl]-5-isoquinolinesulfonamide → N-(2-(Methylamino)ethyl)-5-isoquinolinesulfonamide

HRID 1248762Notes

Reaction equation

HRID 1248762 reaction equation
[CH3:1][N:2]([CH2:10][CH2:11][NH:12][S:13]([C:16]1[C:17]2[CH:18]=[CH:19][N:20]=[CH:21][C:22]=2[CH:23]=[CH:24][CH:25]=1)(=[O:15])=[O:14])CC1C=CC=CC=1.[H][H]>C(O)C.[C].[Pd]>[CH3:1][NH:2][CH2:10][CH2:11][NH:12][S:13]([C:16]1[C:17]2[CH:18]=[CH:19][N:20]=[CH:21][C:22]=2[CH:23]=[CH:24][CH:25]=1)(=[O:15])=[O:14]

Participants

5

Reactant 2

HCID 20254295N-[2-(N-methyl-N-benzylamino)ethyl]-5-isoquinolinesulfonamideHCID 178418361HCID 178418361, compound

Product 1

HCID 3540N-(2-(Methylamino)ethyl)-5-isoquinolinesulfonamideYield 64%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

In 100 ml of ethanol was dissolved 2.0 g of N-[2-(N-methyl-N-benzylamino)ethyl]-5-isoquinolinesulfonamide, i.e., Compound (65) as obtained in Example 16, and to the solution was added 0.2 g of 10% palladium-carbon. Then the solution was vigorously stirred at a temperature of 20° C. to 25° C. in a hydrogen stream of 2.0 to 2.5 atm. for 5 hours. After the palladium-carbon was separated from the reaction solution by filtration, the reaction solution was concentrated to dryness to give 0.95 g of N-(2-methylaminoethyl)-5-isoquinolinesulfonamide, i.e., Compound (14) in a yield of 64%.

Workup

  1. customas obtained in Example 16
  2. customAfter the palladium-carbon was separated from the reaction solution by filtration
  3. concentrationthe reaction solution was concentrated to dryness

Sources & evidence

ORD record
ord-55c5b1fa46c8417482e6b7ffff2235cb
Source dataset
uspto-grants-1985_06
Patent number
US04525589

Reaction notes

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