Putrescine → 6-[(4-Aminobutyl)amino]-3-pyridinecarbonitrile

HRID 2281965Notes

Reaction equation

HRID 2281965 reaction equation
Cl[C:2]1[N:7]=[CH:6][C:5]([C:8]#[N:9])=[CH:4][CH:3]=1.[NH2:10][CH2:11][CH2:12][CH2:13][CH2:14][NH2:15]>>[NH2:10][CH2:11][CH2:12][CH2:13][CH2:14][NH:15][C:2]1[N:7]=[CH:6][C:5]([C:8]#[N:9])=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 1045PutrescineHCID 51520946-Chloro-3-pyridinecarbonitrile

Product 1

HCID 570445896-[(4-Aminobutyl)amino]-3-pyridinecarbonitrile

Conditions

Temperature
170 °C

Procedure

6-Chloro-3-pyridinecarbonitrile (5.0 g) was dissolved in 1,4-diaminobutane (50 ml), and the solution was stirred at 170° C. for 2 hours with heating. Diethyl ether and distilled water were added to the reaction mixture, the layers were separated, and the aqueous layer was extracted with diethyl ether. The aqueous layer was saturated with sodium chloride, and the resulting mixture was extracted with chloroform. The resulting organic layer was dried over anhydrous magnesium sulfate, and filtered, and the filtrate was concentrated under reduced pressure to obtain the title compound (4.77 g).

Workup

  1. temperaturewith heating
  2. distillationDiethyl ether and distilled water
  3. additionwere added to the reaction mixture
  4. customthe layers were separated
  5. extractionthe aqueous layer was extracted with diethyl ether
  6. extractionthe resulting mixture was extracted with chloroform
  7. dry with materialThe resulting organic layer was dried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-d55adc20c14845db9834123deff5324f
Source dataset
uspto-grants-2015_09
Patent number
US09139609B2

Reaction notes

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