Bis(3-aminopropyl)amine → HCID 10892374, compound

HRID 2371845Notes

Reaction equation

HRID 2371845 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH:7]=O.[NH2:9][CH2:10][CH2:11][CH2:12][NH:13][CH2:14][CH2:15][CH2:16][NH2:17].[H][H]>C(O)C.[Pd]>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][NH:9][CH2:10][CH2:11][CH2:12][NH:13][CH2:14][CH2:15][CH2:16][NH:17][CH2:7][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=1

Participants

6

Reactant 3

HCID 5942Bis(3-aminopropyl)amineHCID 142732-PyridinecarboxaldehydeHCID 178418361HCID 178418361, compound2×

Product 1

HCID 10892374HCID 10892374, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

Pyridine-2-carboxaldehyde (4.3 g, 0.04 mole) and 1,5,9-triazanonane (2.6 g, 0.02 mole) [bis(aminopropyl)- amine; available from Aldrich Chemical Company] were dissolved in ca. 60 ml of absolute ethanol and warmed (ca. 50° C.) with stirring for 10 minutes. The solution was hydrogenated at room temperature over 1.5 g of 5% Pd on charcoal in an atmosphere of hydrogen. After the calculated amount of hydrogen (0.04 mole; ca. 0.90 1 at 25° C. and 1 atm. pressure) had been consumed, the charcoal catalyst was removed by filtration, and dry HCl gas was bubbled into the solution until no further white precipitate formed. After removing the precipitate by filtration of the cooled solution, the product was washed with absolute ethanol, dried, and recrystallized from 95% ethanol.

Workup

  1. customthe charcoal catalyst was removed by filtration, and dry HCl gas
  2. customwas bubbled into the solution until no further white precipitate
  3. customformed
  4. customAfter removing the precipitate
  5. filtrationby filtration of the cooled solution
  6. washthe product was washed with absolute ethanol
  7. customdried
  8. customrecrystallized from 95% ethanol

Sources & evidence

ORD record
ord-17c90d072c5a4c2c8b29ee12d344e4d6
Source dataset
uspto-grants-1992_03
Patent number
US05096724

Reaction notes

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