Reaction #156201

Reaction equation

hydrogen chloride

Sodium iodide

N-(3-chloropropyl)-N-(2-methylbenzyl)-N-(2-pyridin-3-ylethyl)amine

Potassium carbonate

6-hydroxyquinoline

→

title compound

N-(2-methylbenzyl)-N-(2-pyridin-3-ylethyl)-N-[3-(quinolin-6-yloxy)propyl]amine trihydrochloride

Solvents

ethyl acetate

ethyl acetate

DMF

Conditions

Workup

1. 1
   TemperatureThe reaction mixture was cooled to room temperature
2. 2
   workup.STIRRINGstirred at 60° C. for 24 hours
3. 3
   Extractionthe extraction with ethyl acetate
4. 4
   WashThe organic layer was washed with a saturated sodium chloride aqueous solution
5. 5
   Dryingdried over anhydrous sodium sulfate
6. 6
   Concentrationconcentrated under reduced pressure
7. 7
   OtherThe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=1:1→0:1)
8. 8
   Othercondensed under reduced pressure
9. 9
   workup.STIRRINGthe liquid was stirred at room temperature
10. 10
    OtherThe precipitated insoluble product was separated
11. 11
    Washwashed with ether
12. 12
    Otherdried

Procedure

Sodium iodide (113 mg) was added to a DMF solution (5 ml) of N-(3-chloropropyl)-N-(2-methylbenzyl)-N-(2-pyridin-3-ylethyl)amine (151 mg), and stirred at 60° C. for 1 hours. The reaction mixture was cooled to room temperature. Potassium carbonate (104 mg) and 6-hydroxyquinoline (87 mg) were then added to the reaction mixture and stirred at 60° C. for 24 hours. The reaction mixture was added to ice water, and the extraction with ethyl acetate was performed. The organic layer was washed with a saturated sodium chloride aqueous solution, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=1:1→0:1). The purified product was condensed under reduced pressure. A 4N-hydrogen chloride in ethyl acetate solution (0.014 ml) was added to a ethyl acetate solution (1 ml) of the residue, and the liquid was stirred at room temperature. The precipitated insoluble product was separated, washed with ether, and dried to give the title compound (7.6 mg) as a brown powder.

Source