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1,8-Diazabicyclo(5.4.0)undec-7-ene → 1-(3-(1-(4-Methoxy-2,6-dimethylphenylsulfonyl)piperidin-2-yl)propylsulfonyl)-4-(1-methylpiperidin-4-yl)piperazine

HRID 1643461
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1643461
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH3:9])[C:6]([S:10]([N:13]2[CH2:18][CH2:17][CH2:16][CH2:15][CH:14]2[CH2:19][CH2:20][CH2:21][S:22]([O:25]C2C(F)=C(F)C(F)=C(F)C=2F)(=O)=[O:23])(=[O:12])=[O:11])=[C:5]([CH3:37])[CH:4]=1.[CH3:38][N:39]1[CH2:44][CH2:43][CH:42]([N:45]2[CH2:50][CH2:49][NH:48][CH2:47][CH2:46]2)[CH2:41][CH2:40]1.N12CCCN=C1CCCCC2.C(=O)(O)[O-].[Na+]>O1CCCC1.C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH3:37])[C:6]([S:10]([N:13]2[CH2:18][CH2:17][CH2:16][CH2:15][CH:14]2[CH2:19][CH2:20][CH2:21][S:22]([N:48]2[CH2:47][CH2:46][N:45]([CH:42]3[CH2:43][CH2:44][N:39]([CH3:38])[CH2:40][CH2:41]3)[CH2:50][CH2:49]2)(=[O:23])=[O:25])(=[O:11])=[O:12])=[C:7]([CH3:9])[CH:8]=1
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Komponenten

7

Edukt 4

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 516892Sodium BicarbonateHCID 5663241-(1-Methyl-4-piperidinyl)piperazineHCID 59367793Perfluorophenyl 3-(1-(4-methoxy-2,6-dimethylphenylsulfonyl)piperidin-2-yl)propane-1-sulfonate

Produkt 1

HCID 593677251-(3-(1-(4-Methoxy-2,6-dimethylphenylsulfonyl)piperidin-2-yl)propylsulfonyl)-4-(1-methylpiperidin-4-yl)piperazine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Perfluorophenyl 3-(1-(4-methoxy-2,6-dimethylphenylsulfonyl)piperidin-2-yl)propane-1-sulfonate (40 mg, 0.07 mmol) and 1-(1-methyl-4-piperidinyl)piperazine (25 mg, 0.14 mmol) were dissolved in tetrahydrofuran (10 ml), 1,8-diazabicyclo[5.4.0]undec-7-ene (0.03 ml, 0.21 mmol) was added under an inert gas and the mixture was refluxed for 1 h and stirred at room temperature for 15 h. Methylene chloride and saturated sodium bicarbonate solution (10 ml of each) were added, the phases were separated and the aqueous phases were extracted with methylene chloride (20 ml). The combined organic phases were dried over sodium sulfate and concentrated in vacuo. The crude product was purified by column chromatography (silica gel) with ethyl acetate/methanol/ammonia (25 aq) (200:100:1). Yield: 18 mg (45%). MS, m/z=571.3 [MH]+

Aufarbeitung

  1. temperaturethe mixture was refluxed for 1 h
  2. customthe phases were separated
  3. extractionthe aqueous phases were extracted with methylene chloride (20 ml)
  4. dry with materialThe combined organic phases were dried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified by column chromatography (silica gel) with ethyl acetate/methanol/ammonia (25 aq) (200:100:1)

Quellen und Nachweise

ORD-Eintrag
ord-c21699cf1e1847769e1f381d4521bfb5
Quelldatensatz
uspto-grants-2012_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08119805B2

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