Cadaverine → N-(5-Aminopentyl)benzamide

HRID 353818

Reaction equation

HRID 353818 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][NH2:7].[C:8](N)(=[O:15])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>>[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][NH:7][C:8](=[O:15])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

3

Reactant 2

HCID 273CadaverineHCID 2331Benzamide

Product 1

HCID 345353N-(5-Aminopentyl)benzamideYield 70.6%

Procedure

Under an argon atmosphere, 1,5-diaminopentane (25 g, 0.24 mol) and benzamide (9.9 g, 0.081 mol) were combined and heated at reflux overnight. The reaction mixture was concentrated under vacuum to remove the excess diamine. The residue was distilled at about 210° C. at 12 torr (16×102 pascals) to provide 11.8 g of N-(5-aminopentyl)benzamide as a colorless oil.

Workup

  1. temperatureheated
  2. temperatureat reflux overnight
  3. concentrationThe reaction mixture was concentrated under vacuum
  4. customto remove the excess diamine
  5. distillationThe residue was distilled at about 210° C. at 12 torr (16×102 pascals)

Sources & evidence

ORD record
ord-b381b192013040f686acf978ecc3b618
Source dataset
uspto-grants-2004_06
Patent number
US06756382B2

Linked notes

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