Diisopropylethylamine → 3-Phenylsulfonyl-8-piperazin-1-yl-quinoline hydrochloride

HRID 1010597

Reaktionsgleichung

Reaktionsgleichung von HRID 1010597
C[N:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:9]=[CH:10][CH:11]=[C:12]3[C:17]=2[N:16]=[CH:15][C:14]([S:18]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)(=[O:20])=[O:19])=[CH:13]3)[CH2:4][CH2:3]1.[Cl:27]C(OC(Cl)C)=O.C(N(CC)C(C)C)(C)C>ClCCCl>[ClH:27].[C:21]1([S:18]([C:14]2[CH:15]=[N:16][C:17]3[C:12]([CH:13]=2)=[CH:11][CH:10]=[CH:9][C:8]=3[N:5]2[CH2:6][CH2:7][NH:2][CH2:3][CH2:4]2)(=[O:20])=[O:19])[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Komponenten

5

Edukt 3

HCID 81531DiisopropylethylamineHCID 5213051-Chloroethyl chloroformateHCID 99291628-(4-Methyl-piperazin-1-yl)-3phenylsulfonylquinoline

Produkt 1

HCID 569721413-Phenylsulfonyl-8-piperazin-1-yl-quinoline hydrochlorideAusbeute 52,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 111,2-DichloroethaneLösungsmittel

Versuchsvorschrift

A stirred solution of 8-(4-methyl-piperazin-1-yl)-3-phenylsulfonylquinoline (E1) (0.148 g, 0.4 mmol), 1-chloroethyl chloroformate (0.093 ml, 0.85 mmol) and N,N-diisopropylethylamine (0.148 ml, 0.85 mmol) in 1,2-dichloroethane (9 ml) was heated at reflux for 1.25 h under argon. The reaction mixture was cooled to ambient temperature and concentrated in vacuo to an oil. The oil was purified by chromatography over silica gel eluting with a gradient of methanol/dichloromethane, pooling fractions which contained the major component (Rf 0.9, methanol/dichloromethane 1:19). The purified material was redissolved in methanol (15 ml) and the solution was refluxed for 1 h under argon. The reaction mixture was cooled to ambient temperature and concentrated in vacuo to a solid which was stirred with diethyl ether (5 ml) and filtered to afford the title compound (E2) (0.08 g, 0.21 mmol, 51%);

Aufarbeitung

  1. temperatureat reflux for 1.25 h under argon
  2. concentrationconcentrated in vacuo to an oil
  3. customThe oil was purified by chromatography over silica gel eluting with a gradient of methanol/dichloromethane, pooling fractions which
  4. dissolutionThe purified material was redissolved in methanol (15 ml)
  5. temperaturethe solution was refluxed for 1 h under argon
  6. temperatureThe reaction mixture was cooled to ambient temperature
  7. concentrationconcentrated in vacuo to a solid which
  8. filtrationfiltered

Quellen und Nachweise

ORD-Eintrag
ord-917f359a90da4644b55eb3db208e7a1f
Quelldatensatz
uspto-grants-2011_07
Patentnummer
US07977337B2

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