1,3-Propanediamine → HCID 20041357, compound

HRID 1762491Notes

Reaction equation

HRID 1762491 reaction equation
[N+:1]([C:4]1[CH:11]=[CH:10][C:7]([C:8]#[N:9])=[CH:6][CH:5]=1)([O-:3])=[O:2].[Na].[NH2:13][CH2:14][CH2:15][CH2:16]N>C(O)C.C(OCC)(=O)C>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([C:8]2[NH:13][CH2:14][CH2:15][CH2:16][N:9]=2)=[CH:10][CH:11]=1)([O-:3])=[O:2]

Participants

6

Reactant 3

HCID 4281,3-PropanediamineHCID 120904-NitrobenzonitrileHCID 5360545Sodium

Product 1

HCID 20041357HCID 20041357, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

4-Nitrobenzonitrile (17.76 g) was added to a solution of sodium metal (0.138 g) in dry ethanol (150 ml) at room temperature, and the mixture was stirred for 6 h. To the suspension was added 1,3-diaminopropane (8.88 g) and the mixture was heated under reflux for 4 days. Evaporation of the solvent under reduced pressure gave a solid which was dissolved in hot ethyl acetate (450 ml). The solution was extracted with 2N hydrochloric acid (90 ml, 20 ml). The combined acidic extracts were washed with ethyl acetate (100 ml) and then basified with 5N sodium hydroxide (60 ml). The emulsion was extracted into hot ethyl acetate (250 ml, 2×100 ml), the organic extracts were combined, reduced to about 250 ml by evaporation and hot cyclohexane (125 ml) was added. On cooling the title compound deposited as needles (17.7 g), m.p. 168°-172°.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 4 days
  3. customEvaporation of the solvent under reduced pressure
  4. customgave a solid which
  5. extractionThe solution was extracted with 2N hydrochloric acid (90 ml, 20 ml)
  6. washThe combined acidic extracts were washed with ethyl acetate (100 ml)
  7. extractionThe emulsion was extracted into hot ethyl acetate (250 ml, 2×100 ml)
  8. customreduced to about 250 ml by evaporation and hot cyclohexane (125 ml)
  9. additionwas added
  10. temperatureOn cooling the title compound deposited as needles (17.7 g), m.p. 168°-172°

Sources & evidence

ORD record
ord-533d49fdceed48239e7a84aab7a419f8
Source dataset
uspto-grants-1989_05
Patent number
US04833153

Reaction notes

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