Hydrochloric Acid → HCID 10916261, compound

HRID 722691Notes

Reaction equation

HRID 722691 reaction equation
[OH:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.Cl[C:10]1[C:19]2[C:14](=[CH:15][C:16]([Cl:20])=[CH:17][CH:18]=2)[N:13]=[CH:12][CH:11]=1.Cl.[I-].[K+].Cl.[N:25]1([CH2:31][CH2:32][CH2:33]Cl)[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[Cl:20][C:16]1[CH:15]=[C:14]2[C:19]([C:10]([NH:6][C:5]3[CH:7]=[CH:8][C:2]([O:1][CH2:33][CH2:32][CH2:31][N:25]4[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]4)=[CH:3][CH:4]=3)=[CH:11][CH:12]=[N:13]2)=[CH:18][CH:17]=1

Participants

8

Reactant 6

HCID 313Hydrochloric AcidHCID 4034-AminophenolHCID 4875Potassium Iodide2×HCID 68664,7-DichloroquinolineHCID 11430Potassium CarbonateHCID 79624N-(3-chloropropyl)piperidine hydrochloride

Product 1

HCID 10916261HCID 10916261, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

4-Hydroxyaniline (11 mmol), 4,7-dichloroquinoline (10 mmol), 1 ml of 2N hydrochloric acid, and catalytic amounts of potassium iodide were refluxed in acetone for 12 hours. The product was filtered. The product (5 mmol), 3-piperidinopropylchloride hydrochloride (5 mmol), potassium carbonate (15 mmol), and catalytic amounts of potassium iodide were refluxed in acetone for 22 hours. The product was filtered and purified by flash chromatography (eluent: methylene chloride/petroleum ether/triethylamine (95/25/5)). The solvent was removed under reduced pressure. The residue was crystallized with oxalic acid from diethyl ether/ethanol.

Workup

  1. filtrationThe product was filtered
  2. filtrationThe product was filtered
  3. custompurified by flash chromatography (eluent: methylene chloride/petroleum ether/triethylamine (95/25/5))
  4. customThe solvent was removed under reduced pressure
  5. customThe residue was crystallized with oxalic acid from diethyl ether/ethanol

Sources & evidence

ORD record
ord-50dd0dd15a8a47d1a84fb95529031e35
Source dataset
uspto-grants-2006_11
Patent number
US07138413B1

Reaction notes

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