Hydrochloric Acid → HCID 10916261, compound

HRID 604397Notes

Reaction equation

HRID 604397 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-db83169bc0414a19bb298c3bc6c7d179
Source dataset
uspto-grants-2011_03
Patent number
US07910605B2

Reaction notes

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