Cadaverine → N-(5-Aminopentyl)benzamide

HRID 746502

Reaction equation

HRID 746502 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-6b93c46bf3af424ba9e6805efc66fcec
Source dataset
uspto-grants-2008_07
Patent number
US07393859B2

Linked notes

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