Diethyl Ether → HCID 9870902, Verbindung

HRID 2289520Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2289520
Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([CH3:8])[N:3]=1.[Br:9][C:10]1[CH:15]=[CH:14][C:13]([S:16]([N:19]2[CH2:24][CH2:23][N:22]([C:25]([CH:27]3[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]3)=[O:26])[CH2:21][CH2:20]2)(=[O:18])=[O:17])=[CH:12][CH:11]=1.C(N(CC)CC)C.C(OCC)C>C1COCC1>[Br:9][C:10]1[CH:15]=[CH:14][C:13]([S:16]([N:19]2[CH2:24][CH2:23][N:22]([C:25]([CH:27]3[CH2:32][CH2:31][N:30]([C:2]4[CH:7]=[CH:6][N:5]=[C:4]([CH3:8])[N:3]=4)[CH2:29][CH2:28]3)=[O:26])[CH2:21][CH2:20]2)(=[O:18])=[O:17])=[CH:12][CH:11]=1

Komponenten

6

Edukt 4

HCID 3283Diethyl EtherHCID 8471TriethylamineHCID 4244474-Chloro-2-methylpyrimidineHCID 10669572HCID 10669572, Verbindung

Produkt 1

HCID 9870902HCID 9870902, VerbindungAusbeute 30 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

4-Chloro-2-methylpyrimidine (135 mg) was added to a solution of 1-(4-bromophenylsulphonyl)-4-(4-piperidylcarbonyl)piperazine (415 mg) in THF (15 ml) containing triethylamine (0.2 ml). The mixture was heated under reflux for 16 hours. After cooling, the THF was evaporated. The residue was treated with H2O(20 ml) and the aqueous extracted with ethyl acetate (3×20 ml). The combined organic phases were washed with saturated brine (1×20 ml) dried and evaporated to give an oil which was purified by chromatography on silica gel. Elution with dichloromethane/methanol/0.88 NH3 (96:3:1) gave an oil. Trituration with diethyl ether (10 ml) gave, as a colourless solid, l-(4-bromophenylsulphonyl)-4-[1-(2-methylpyrimidyl)-4-piperidylcarbonyl]piperazine (152 mg), mp 200-202° C.; NMR: 1.39-1.48 (m, 2H), 1.55-1.69 (m, 2H), 2.30 (s, 3H), 2.80-3.00 (m, 7H), 3.45-3.67 (m, 4H), 4.32 (m, 2H), 6.57 (d, 1H), 7.65 (d, 2H), 7.83 (d, 2H), 8.03 (d, 1H); EI-MS m/z 508 (M+H).

Aufarbeitung

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 16 hours
  3. temperatureAfter cooling
  4. customthe THF was evaporated
  5. additionThe residue was treated with H2O(20 ml)
  6. extractionthe aqueous extracted with ethyl acetate (3×20 ml)
  7. washThe combined organic phases were washed with saturated brine (1×20 ml)
  8. customdried
  9. customevaporated
  10. customto give an oil which
  11. customwas purified by chromatography on silica gel
  12. washElution with dichloromethane/methanol/0.88 NH3 (96:3:1)
  13. customgave an oil

Quellen und Nachweise

ORD-Eintrag
ord-2cfb2cdf31f749adbfd2a13757e0805c
Quelldatensatz
uspto-grants-2000_07
Patentnummer
US06093718

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