1,3-Propanediamine → N~1~-(Quinolin-2-yl)propane-1,3-diamine

HRID 365285Notes

Reaction equation

HRID 365285 reaction equation
[CH2:1]([NH2:5])[CH2:2][CH2:3][NH2:4].O1[CH2:10][CH2:9][CH2:8][CH2:7]1.[N:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>>[N:11]1[C:12]2[C:10](=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:9]=[CH:8][C:7]=1[NH:4][CH2:3][CH2:2][CH2:1][NH2:5]

Participants

4

Reactant 3

HCID 4281,3-PropanediamineHCID 1049PyridineHCID 8028Tetrahydrofuran

Product 1

HCID 22118517N~1~-(Quinolin-2-yl)propane-1,3-diamineYield 82%

Procedure

To a solution of propane-1,3-diamine (65.1 ml, 0.764 mol) in dry pyridine (25 ml) kept under an atmosphere of nitrogen 2-chloro-quinoline (25 g, 0.153 mol) was added. The reaction mixture was heated at reflux temperature for 18 h. To the cooled reaction mixture was added tetrahydrofuran (100 ml) and the precipitate was filtered off and washed with tetrahydrofuran (2×50 ml). The solvent was evaporated in vacuo and the residue purified by distillation at 154° C. and 2.5×10-2 mbar affording 25.34 g (82%) of N-(quinolin-2-yl)propane-1,3-diamine as a crystallising oil.

Workup

  1. additionwas added
  2. temperatureThe reaction mixture was heated
  3. temperatureat reflux temperature for 18 h
  4. customTo the cooled reaction mixture
  5. filtrationthe precipitate was filtered off
  6. washwashed with tetrahydrofuran (2×50 ml)
  7. customThe solvent was evaporated in vacuo
  8. distillationthe residue purified by distillation at 154° C.

Sources & evidence

ORD record
ord-8d6f890a37c14fd4a642ba4963973dd0
Source dataset
uspto-grants-2000_10
Patent number
US06127343

Reaction notes

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