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

HRID 69019

반응식

HRID 69019 반응식
[I-].[Na+].[Cl:3][CH2:4][CH2:5][CH2:6][N:7]([CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[CH3:23])[CH2:8][CH2:9][C:10]1[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=1.C(=O)([O-])[O-].[K+].[K+].[OH:30][C:31]1[CH:32]=[C:33]2[C:38](=[CH:39][CH:40]=1)[N:37]=[CH:36][CH:35]=[CH:34]2.[ClH:41]>C(OCC)(=O)C.CN(C=O)C>[ClH:3].[ClH:41].[ClH:3].[CH3:23][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=1[CH2:16][N:7]([CH2:8][CH2:9][C:10]1[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=1)[CH2:6][CH2:5][CH2:4][O:30][C:31]1[CH:32]=[C:33]2[C:38](=[CH:39][CH:40]=1)[N:37]=[CH:36][CH:35]=[CH:34]2

참가 물질

8

반응물 5

HCID 313Hydrochloric AcidHCID 5238Sodium IodideHCID 113746-HydroxyquinolineHCID 11430Potassium CarbonateHCID 70656976N-(3-chloropropyl)-N-(2-methylbenzyl)-N-(2-pyridin-3-ylethyl)amine

생성물 1

HCID 66959964N-(2-methylbenzyl)-N-(2-pyridin-3-ylethyl)-N-[3-(quinolin-6-yloxy)propyl]amine trihydrochloride

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매2회

반응 조건

온도
60 °C

실험 절차

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.

후처리

  1. temperatureThe reaction mixture was cooled to room temperature
  2. stirringstirred at 60° C. for 24 hours
  3. extractionthe extraction with ethyl acetate
  4. washThe organic layer was washed with a saturated sodium chloride aqueous solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=1:1→0:1)
  8. customcondensed under reduced pressure
  9. stirringthe liquid was stirred at room temperature
  10. customThe precipitated insoluble product was separated
  11. washwashed with ether
  12. customdried

출처 및 근거

ORD 기록
ord-5ebe8529af324a4c958c08808cf03096
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08822453B2

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