N,N-Dimethyl-1,3-propanediamine → N-(3-dimethylaminopropyl)-5-isoquinolinesulfonamide

HRID 638373Notes

Reaction equation

HRID 638373 reaction equation
[CH3:1][N:2]([CH3:7])[CH2:3][CH2:4][CH2:5][NH2:6].C(N(CC)CC)C.[CH:15]1[C:24]2[CH:23]=[CH:22][CH:21]=[C:20]([S:25](Cl)(=[O:27])=[O:26])[C:19]=2[CH:18]=[CH:17][N:16]=1>C(Cl)(Cl)Cl>[CH3:1][N:2]([CH3:7])[CH2:3][CH2:4][CH2:5][NH:6][S:25]([C:20]1[C:19]2[CH:18]=[CH:17][N:16]=[CH:15][C:24]=2[CH:23]=[CH:22][CH:21]=1)(=[O:26])=[O:27]

Participants

5

Reactant 3

HCID 7993N,N-Dimethyl-1,3-propanediamineHCID 8471TriethylamineHCID 33716555-Isoquinolinesulfonyl chloride

Product 1

HCID 20254274N-(3-dimethylaminopropyl)-5-isoquinolinesulfonamideYield 71%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent4×

Procedure

In 50 ml of a chloroform solution containing 1.4 g of 3-dimethylaminopropylamine and 1.4 g of triethylamine was added dropwise 30 ml of a chloroform solution containing 2.6 g of 5-isoquinolinesulfonyl chloride under cooling with ice. After the dropwise addition of the chloroform solution, the mixed solution was stirred at a temperature of 2° C. to 10° C. for four hours, and the reaction mixture solution was washed with water and dried with anhydrous magnesium sulfate. After the chloroform was distilled therefrom, the residue obtained was subjected to a silica gel column chromatography (silica gel: 70 g; solvent: chloroform) to give 2.38 g of N-(3-dimethylaminopropyl)-5-isoquinolinesulfonamide, i.e., Compound (17) in a yield of 71%.

Workup

  1. temperatureunder cooling with ice
  2. washthe reaction mixture solution was washed with water
  3. dry with materialdried with anhydrous magnesium sulfate
  4. distillationAfter the chloroform was distilled
  5. customthe residue obtained

Sources & evidence

ORD record
ord-89973c8d8ef842b4b10720168073a545
Source dataset
uspto-grants-1985_12
Patent number
US04560755

Reaction notes

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