Sodium Hydroxide → 4-[3-[[2-[4-(4,6-Dimethyl-2-pyridyl)piperazin-1-yl]-5-nitro-phenyl]methoxy]propyl]morpholine

HRID 37865

Reaktionsgleichung

Reaktionsgleichung von HRID 37865
[OH-].[Na+].[CH3:3][C:4]1[CH:9]=[C:8]([CH3:10])[N:7]=[C:6]([N:11]2[CH2:16][CH2:15][N:14]([C:17]3[CH:22]=[CH:21][C:20]([N+:23]([O-:25])=[O:24])=[CH:19][C:18]=3[CH2:26][OH:27])[CH2:13][CH2:12]2)[CH:5]=1.Cl[CH2:29][CH2:30][CH2:31][N:32]1[CH2:37][CH2:36][O:35][CH2:34][CH2:33]1>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1>[CH3:3][C:4]1[CH:9]=[C:8]([CH3:10])[N:7]=[C:6]([N:11]2[CH2:16][CH2:15][N:14]([C:17]3[CH:22]=[CH:21][C:20]([N+:23]([O-:25])=[O:24])=[CH:19][C:18]=3[CH2:26][O:27][CH2:29][CH2:30][CH2:31][N:32]3[CH2:37][CH2:36][O:35][CH2:34][CH2:33]3)[CH2:13][CH2:12]2)[CH:5]=1

Komponenten

6

Edukt 3

HCID 14798Sodium HydroxideHCID 958344-(3-Chloropropyl)morpholineHCID 66851343[2-[4-(4,6-Dimethyl-2-pyridyl)piperazin-1-yl]-5-nitro-phenyl]methanol

Produkt 1

HCID 668515124-[3-[[2-[4-(4,6-Dimethyl-2-pyridyl)piperazin-1-yl]-5-nitro-phenyl]methoxy]propyl]morpholineAusbeute 80,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 94433Tetrabutylammonium hydrogen sulfateKatalysatorHCID 1140TolueneLösungsmittel

Versuchsvorschrift

Aqueous sodium hydroxide (50% w/w, 10 g, 125 mmol) and tetrabutylammonium hydrogen sulfate (0.20 g) were added successively to a solution of {2-[4-(4,6-dimethyl-pyridin-2-yl)-piperazin-1-yl]-5-nitro-phenyl}-methanol (0.50 g, 1.46 mmol) in toluene (5 mL). The mixture was heated to reflux with vigorous stirring for 45 min then 4-(3-chloro-propyl)-morpholine (0.50 g, 3.00 mmol) was added and reflux continued for 28 h. The reaction mixture was cooled and the organic phase separated. The aqueous phase was extracted with ethyl acetate (3×5 mL). The organic phases were combined, washed with water and brine, dried over anhydrous sodium sulfate, filtered and concentrated under vacuum to give a residue which was purified by preparative TLC eluting with 2% methanol in chloroform to afford 4-(3-{2-[4-(4,6-dimethyl-pyridin-2-yl)-piperazin-1-yl]-5-nitro-benzyloxy}-propyl)-morpholine (550 mg, 80%) as a solid.

Aufarbeitung

  1. temperatureThe mixture was heated
  2. temperatureto reflux
  3. temperaturereflux
  4. waitcontinued for 28 h
  5. temperatureThe reaction mixture was cooled
  6. customthe organic phase separated
  7. extractionThe aqueous phase was extracted with ethyl acetate (3×5 mL)
  8. washwashed with water and brine
  9. dry with materialdried over anhydrous sodium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated under vacuum
  12. customto give a residue which
  13. customwas purified by preparative TLC
  14. washeluting with 2% methanol in chloroform

Quellen und Nachweise

ORD-Eintrag
ord-a1b85dc1a63c43578fd8840a4ea5c503
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08524705B2

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