Cadaverine → N-(5-aminopentyl)naphthalene-1-sulfonamide

HRID 50611Notes

Reaction equation

HRID 50611 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][NH2:7].[C:8]1([S:18](Cl)(=[O:20])=[O:19])[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:11]=[CH:10][CH:9]=1>C(#N)C>[C:8]1([S:18]([NH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][NH2:7])(=[O:20])=[O:19])[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:11]=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 273CadaverineHCID 665601-Naphthalenesulfonyl chloride

Product 1

HCID 4303N-(5-aminopentyl)naphthalene-1-sulfonamideYield 84.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Under ice cooling, 7.91 g of 1,5-diaminopentane was added dropwise with 240 mL of acetonitrile solution in which 1.75 g of 1-naphthalenesulfonyl chloride was dissolved, and the mixture was stirred at room temperature for 1 hour. The reaction mixture was evaporated under reduced pressure, and the residue was added with 500 mL of water and extracted with dichloromethane. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure to obtain 1.90 g of 5-(1-naphthalenesulfonyl)aminopentylamine.

Workup

  1. dissolutionwas dissolved
  2. customThe reaction mixture was evaporated under reduced pressure
  3. additionthe residue was added with 500 mL of water
  4. extractionextracted with dichloromethane
  5. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  6. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-e8b2e0abf9594c33858deb2304f39cd4
Source dataset
uspto-grants-2004_03
Patent number
US06713473B1

Reaction notes

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