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

HRID 37865

반응식

HRID 37865 반응식
[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

참가 물질

6

반응물 3

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

생성물 1

HCID 668515124-[3-[[2-[4-(4,6-Dimethyl-2-pyridyl)piperazin-1-yl]-5-nitro-phenyl]methoxy]propyl]morpholine수율 80.2%

시약·촉매·용매 2

HCID 94433Tetrabutylammonium hydrogen sulfate촉매HCID 1140Toluene용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-a1b85dc1a63c43578fd8840a4ea5c503
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08524705B2

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