Putrescine → N-(4-Aminobutyl)isoquinoline-5-sulfonamide

HRID 1248749Notes

Reaction equation

HRID 1248749 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][NH2:6].[CH:7]1[C:16]2[CH:15]=[CH:14][CH:13]=[C:12]([S:17](Cl)(=[O:19])=[O:18])[C:11]=2[CH:10]=[CH:9][N:8]=1.CO.C(Cl)(Cl)Cl>C(Cl)(Cl)Cl>[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][NH:6][S:17]([C:12]1[C:11]2[CH:10]=[CH:9][N:8]=[CH:7][C:16]=2[CH:15]=[CH:14][CH:13]=1)(=[O:18])=[O:19]

Participants

5

Reactant 3

HCID 1045PutrescineHCID 33716555-Isoquinolinesulfonyl chlorideHCID 21584188Chloroform methanol

Product 1

HCID 13231162N-(4-Aminobutyl)isoquinoline-5-sulfonamideYield 62%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent3×

Procedure

In 200 ml of chloroform was dissolved 8.8 g of 1,4-diaminobutane, and to the solution was added dropwise 100 ml of a chloroform solution containing 4.55 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 20° C. to 25° C. for two hours, and then the reaction solution was extracted with a 10% aqueous hydrochloric acid solution. The pH of the aqueous layer was adjusted to 10 with a 10% aqueous sodium hydroxide solution, and the aqueous layer was extracted with chloroform. The chloroform layer extracted was washed with water and dried with anhydrous potassium carbonate. Then the chloroform was distilled from the chloroform layer, and the residue obtained was subjected to a column chromatography [silica gel: 200 g; developing solvent: 2% methanol/chloroform (volume ratio)] to give 3.46 g of N-(4-aminobutyl)-5-isoquinolinesulfonamide, i.e., Compound (3) as an oily substance in a yield of 62%.

Workup

  1. temperatureunder cooling with ice
  2. extractionthe reaction solution was extracted with a 10% aqueous hydrochloric acid solution
  3. extractionthe aqueous layer was extracted with chloroform
  4. extractionThe chloroform layer extracted
  5. washwas washed with water
  6. dry with materialdried with anhydrous potassium carbonate
  7. distillationThen the chloroform was distilled from the chloroform layer
  8. customthe residue obtained

Sources & evidence

ORD record
ord-bb6d4ef293ee444aa3b58e2413be48cd
Source dataset
uspto-grants-1985_06
Patent number
US04525589

Reaction notes

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