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

HRID 1263339Notes

Reaction equation

HRID 1263339 reaction equation
[CH3:1][N:2]([CH2:10][CH2:11][NH2:12])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.C(N(CC)CC)C.[CH:20]1[C:29]2[CH:28]=[CH:27][CH:26]=[C:25]([S:30](Cl)(=[O:32])=[O:31])[C:24]=2[CH:23]=[CH:22][N:21]=1.C(Cl)(Cl)Cl>C(Cl)Cl>[CH3:1][N:2]([CH2:10][CH2:11][NH:12][S:30]([C:25]1[C:24]2[CH:23]=[CH:22][N:21]=[CH:20][C:29]=2[CH:28]=[CH:27][CH:26]=1)(=[O:31])=[O:32])[CH2:3][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

6

Reactant 4

HCID 6212ChloroformHCID 8471TriethylamineHCID 3014812(2-Aminoethyl)(benzyl)methylamineHCID 33716555-Isoquinolinesulfonyl chloride

Product 1

HCID 20254295N-[2-(N-methyl-N-benzylamino)ethyl]-5-isoquinolinesulfonamideYield 84%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

In 70 ml of methylene chloride were dissolved 3.24 g of 2-(N-methyl-N-benzylamino)ethylamine and 2.0 g of triethylamine, and to the solution was added dropwise 50 ml of a methylene chloride solution containing 3.0 g of 5-isoquinolinesulfonyl chloride under cooling with ice. After the dropwise addition of the methylene chloride solution, the mixed solution was stirred at a temperature of 15° C. to 25° C. for one hour, and then the reaction solution was washed with water and extracted with a 10% aqueous hydrochloric acid solution. The aqueous layer was washed with chloroform, rendered alkaline with a 1N aqueous sodium hydroxide solution, extracted with chloroform, and then the chloroform layer was washed with water, dried with anhydrous magnesium sulfate and the chloroform was distilled therefrom under reduced pressure. The residue thus obtained was subjected to a silica gel column chromatography (silica gel: 100 g; solvent: chloroform) to give 3.84 g of N-[2-(N-methyl-N-benzylamino)ethyl]-5-isoquinolinesulfonamide, i.e., Compound (65) in a yield of 84%.

Workup

  1. temperatureunder cooling with ice
  2. washthe reaction solution was washed with water
  3. extractionextracted with a 10% aqueous hydrochloric acid solution
  4. washThe aqueous layer was washed with chloroform
  5. extractionextracted with chloroform
  6. washthe chloroform layer was washed with water
  7. dry with materialdried with anhydrous magnesium sulfate
  8. distillationthe chloroform was distilled
  9. customThe residue thus obtained

Sources & evidence

ORD record
ord-dc610d0439334e88aff7b2f22a021553
Source dataset
uspto-grants-1984_06
Patent number
US04456757

Reaction notes

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