N-[3-(N-phenyl-N-pyrid-2-ylamino)propyl]phthalimide → 2-[N-(3-aminopropyl)-N-phenylamino]pyridine

HRID 2308985Notes

Reaction equation

HRID 2308985 reaction equation
[C:1]1([N:7]([CH2:14][CH2:15][CH2:16][N:17]2C(=O)C3=CC=CC=C3C2=O)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>Cl>[NH2:17][CH2:16][CH2:15][CH2:14][N:7]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=1)[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

3

Reactant 1

HCID 20186606N-[3-(N-phenyl-N-pyrid-2-ylamino)propyl]phthalimide

Product 1

HCID 198610732-[N-(3-aminopropyl)-N-phenylamino]pyridine

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A mixture of N-[3-(N-phenyl-N-pyrid-2-ylamino)-propyl]phthalimide, (3.1 g) and conc. hydrochloric acid (30 ml) were heated under reflux for 21 hr. Phthalic acid was filtered off on cooling and the solvent was evaporated from the filtrate. The residue was dissolved in water and the solution extracted at pH 1 with chloroform. The pH was raised to pH 13 (NaOH) and the solution extracted again with ether. The ether extracts were dried (K2CO3) and the ether was evaporated to give 2-[N-(3-aminopropyl)-N-phenylamino]pyridine, 1.84 g as an oil.

Workup

  1. temperaturewere heated
  2. temperatureunder reflux for 21 hr
  3. filtrationPhthalic acid was filtered off
  4. temperatureon cooling
  5. customthe solvent was evaporated from the filtrate
  6. dissolutionThe residue was dissolved in water
  7. extractionthe solution extracted at pH 1 with chloroform
  8. temperatureThe pH was raised to pH 13 (NaOH)
  9. extractionthe solution extracted again with ether
  10. dry with materialThe ether extracts were dried (K2CO3)
  11. customthe ether was evaporated

Sources & evidence

ORD record
ord-e976790400674f419018f53e0eae5d9a
Source dataset
uspto-grants-1987_09
Patent number
US04692456

Reaction notes

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