Propylamine → HCID 22667105, compound

HRID 1375800Notes

Reaction equation

HRID 1375800 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][CH:7]=[C:6]2[O:15][C:16]1[C:22]([CH3:23])=[CH:21][C:19]([NH2:20])=[C:18]([CH3:24])[CH:17]=1.ClC(Cl)(O[C:29](=[O:35])OC(Cl)(Cl)Cl)Cl.[CH2:37]([NH2:40])[CH2:38][CH3:39].C(=O)([O-])O.[Na+]>C(Cl)(Cl)Cl.C(N(CC)CC)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][CH:7]=[C:6]2[O:15][C:16]1[C:22]([CH3:23])=[CH:21][C:19]([NH:20][C:29]([NH:40][CH2:37][CH2:38][CH3:39])=[O:35])=[C:18]([CH3:24])[CH:17]=1

Participants

7

Reactant 4

HCID 7852PropylamineHCID 94429TriphosgeneHCID 516892Sodium BicarbonateHCID 218904214-((6,7-Dimethoxyquinolin-4-yl)oxy)-2,5-dimethylaniline

Product 1

HCID 22667105HCID 22667105, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolvent2×HCID 8471TriethylamineSolvent

Procedure

4-[(6,7-Dimethoxy-4-quinolyl)oxy]-2,5-dimethylaniline (150 mg) was dissolved in chloroform (13 ml) and triethylamine (1.5 ml), and a solution of triphosgene (151 mg) in chloroform was then added to the solution. The mixture was heated under reflux for 5 min. Next, n-propylamine (33 mg) was added to the reaction solution, and the mixture was heated under reflux for additional 2 hr. A saturated aqueous sodium hydrogencarbonate solution was added to the reaction solution, and the mixture was supported on diatomaceous earth, followed by extraction with chloroform. The solvent was removed by distillation under the reduced pressure. The residue was purified by chromatography on silica gel by development with chloroform/acetone (4/1) to give 178 mg (yield 95%) of the title compound.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 5 min
  3. temperaturethe mixture was heated
  4. temperatureunder reflux for additional 2 hr
  5. extractionfollowed by extraction with chloroform
  6. customThe solvent was removed by distillation under the reduced pressure
  7. customThe residue was purified by chromatography on silica gel by development with chloroform/acetone (4/1)

Sources & evidence

ORD record
ord-4fc0ef23563f40f18249e4c15c512a7b
Source dataset
uspto-grants-2007_01
Patent number
US07169789B2

Reaction notes

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