4-Chlorobenzenesulfonyl chloride → HCID 9846568, Verbindung

HRID 1249719Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1249719
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8](Cl)(=[O:10])=[O:9])=[CH:4][CH:3]=1.Cl.Cl.Cl.[CH3:15][C:16]1[N:21]=[C:20]([N:22]2[CH2:27][CH2:26][N:25]([CH2:28][CH:29]3[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]3)[CH2:24][CH2:23]2)[CH:19]=[CH:18][N:17]=1.C(N(CC)CC)C>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:32]2[CH2:33][CH2:34][CH:29]([CH2:28][N:25]3[CH2:26][CH2:27][N:22]([C:20]4[CH:19]=[CH:18][N:17]=[C:16]([CH3:15])[N:21]=4)[CH2:23][CH2:24]3)[CH2:30][CH2:31]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 73984-Chlorobenzenesulfonyl chlorideHCID 8471TriethylamineHCID 18328910HCID 18328910, Verbindung

Produkt 1

HCID 9846568HCID 9846568, VerbindungAusbeute 76,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel3×

Versuchsvorschrift

A solution of 4-chlorophenylsulphonyl chloride (1.78 g) in methylene chloride (10 ml) was added dropwise over 15 minutes to a mixture of 4-[1-(2-methylpyrimidin-4-yl)piperazine-4-ylmethyl]piperidine trihydrochloride (2.78 g) and triethylamine (6.72 ml) in dichloromethane (40 ml) at 0° C. The solution was stirred at ambient temperature for 18 hours. The solution was diluted with dichloromethane and washed with water, dried (Na2SO4) and evaporated. The residue was purified by chromatography eluting with 4% methanol in dichloromethane. Recrystallisation from ethyl acetate/hexane gave, as a solid 1-(4-chlorophenylsulphonyl)-4-[1-(2-methylpyrimidin-4-yl)piperazin-4ylmethyl]piperidine (2.50 g), mp 191-193° C. (decomp.).

Aufarbeitung

  1. washwashed with water
  2. dry with materialdried (Na2SO4)
  3. customevaporated
  4. customThe residue was purified by chromatography
  5. washeluting with 4% methanol in dichloromethane
  6. customRecrystallisation from ethyl acetate/hexane

Quellen und Nachweise

ORD-Eintrag
ord-0b85241f0333445599018e83613de919
Quelldatensatz
uspto-grants-2002_01
Patentnummer
US06335341B1

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