1-Propanol → HCID 86754296, compound

HRID 583116Notes

Reaction equation

HRID 583116 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][N:12]1[CH2:17][CH2:16][N:15]([C:18]2[CH:19]=[C:20]([CH:27]=[CH:28][C:29]=2[O:30][CH3:31])[CH2:21][NH:22][O:23][CH:24]=[C:25]=[O:26])[CH2:14][CH2:13]1.[Cl:32][C:33]1[C:34](=[O:43])[NH:35][N:36]=[C:37]([O:40][CH2:41][CH3:42])[C:38]=1Cl.C(N(CC)CC)C.C(O)CC>O>[Cl:32][C:33]1[C:34](=[O:43])[NH:35][N:36]=[C:37]([O:40][CH2:41][CH3:42])[C:38]=1[N:22]([O:23][CH:24]=[C:25]=[O:26])[CH2:21][C:20]1[CH:27]=[CH:28][C:29]([O:30][CH3:31])=[C:18]([N:15]2[CH2:16][CH2:17][N:12]([CH2:11][C:2]3[CH:3]=[CH:4][C:5]4[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=4)[N:1]=3)[CH2:13][CH2:14]2)[CH:19]=1

Participants

6

Reactant 4

HCID 10311-PropanolHCID 8471TriethylamineHCID 15079010HCID 15079010, compoundHCID 86754294HCID 86754294, compound

Product 1

HCID 86754296HCID 86754296, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture comprising 2.4 g of 3-[4-(2-quinolylmethyl)-piperazin-1-yl]-carbonylmethoxy-4-methoxybenzylamine, 1 g of 4,5-dichloro-6-ethoxy-3(2H)-pyridazinone, 580 mg of triethylamine, 10 ml of propanol and 10 ml of water, was refluxed under heating with stirring overnight. The solvent was distilled off under reduced pressure, and the residue was extracted with chloroform. The organic layer was washed with an aqueous potassium carbonate solution and then dried over anhydrous sodium sulfate. Then, the solvent was distilled off. The obtained residue was purified by silica gel column chromatography (ethyl acetate:methanol=6:1→chloroform:methanol=12:1) and then crystallized from diethyl ether to obtain 1.5 g of the above-identified compound as white crystals.

Workup

  1. temperaturewas refluxed
  2. temperatureunder heating
  3. distillationThe solvent was distilled off under reduced pressure
  4. extractionthe residue was extracted with chloroform
  5. washThe organic layer was washed with an aqueous potassium carbonate solution
  6. dry with materialdried over anhydrous sodium sulfate
  7. distillationThen, the solvent was distilled off
  8. customThe obtained residue was purified by silica gel column chromatography (ethyl acetate:methanol=6:1→chloroform:methanol=12:1)
  9. customcrystallized from diethyl ether

Sources & evidence

ORD record
ord-2f3d9474f9d049bbb138f3f22315b8e5
Source dataset
uspto-grants-1999_07
Patent number
US05929074

Reaction notes

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