Cadaverine → N-(5-Aminopentyl)benzamide

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

Reactant 2

HCID 273Cadaverine

HCID 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

temperatureheated
temperatureat reflux overnight
concentrationThe reaction mixture was concentrated under vacuum
customto remove the excess diamine
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
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06756382B2

Reaction notes

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