Hydrochloric Acid → Hydrochloric Acid

HRID 555321

Reaktionsgleichung

Reaktionsgleichung von HRID 555321
[H-].[Na+].[Cl:3][C:4]1[CH:5]=[CH:6][C:7]2[NH:8][C:9]3[C:14]([C:15]=2[CH:16]=1)=[CH:13][CH:12]=[CH:11][CH:10]=3.[O:17]1[CH2:19][CH:18]1[CH2:20]OS(C1C=CC=C([N+]([O-])=O)C=1)(=O)=O.[CH:34]1([N:40]2[CH2:45][CH2:44][NH:43][CH2:42][CH2:41]2)[CH2:39][CH2:38][CH2:37][CH2:36][CH2:35]1.[ClH:46]>C1COCC1>[Cl:3][C:4]1[CH:5]=[CH:6][C:7]2[N:8]([CH2:19][CH:18]([OH:17])[CH2:20][N:43]3[CH2:44][CH2:45][N:40]([CH:34]4[CH2:39][CH2:38][CH2:37][CH2:36][CH2:35]4)[CH2:41][CH2:42]3)[C:9]3[C:14]([C:15]=2[CH:16]=1)=[CH:13][CH:12]=[CH:11][CH:10]=3.[ClH:46]

Komponenten

8

Edukt 5

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 872981-CyclohexylpiperazineHCID 286836(Oxiran-2-yl)methyl 3-nitrobenzene-1-sulfonateHCID 5203023-Chlorocarbazole

Produkt 2

HCID 313Hydrochloric AcidHCID 66742182(+/-)-1-(3-Chlorocarbazol-9-yl)-3-(4-cyclohexylpiperazin-1-yl)propan-2-ol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel3×

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

A solution of NaH (0.026 g, 0.60 mmol, 55% in mineral oil) is added into a solution of 3-chloro-9H-carbazole (0.100 g, 0.50 mmol) in anhydrous THF (5 mL). After 30 min of stirring at rt a solution of (±)-3-nitro-benzenesulfonic acid oxiranylmethyl ester in anhydrous THF (0.5 mL) is added. After 90 min of stirring at rt a solution of 1-cyclohexyl piperazine (0.25 g, 1.50 mmol) in anhydrous THF (1 mL) is then added. The resulting mixture is allowed to stir at 60° C. for 15 hours. The reaction mixture is quenched with brine (15 mL) and extracted with Et2O (50 mL+2×25 mL). After drying over MgSO4, evaporation under reduced pressure, the crude compound is purified via flash chromatography on a 3×24 cm2 SiO2 column using EtOAc/MeOH (8/1) and (4/1) as eluant. A solution of the purified above compound (0.088 g, 0.21 mmol, 41%) is treated with HCl (1M in Et2O) to give the title compound hydrochloride (0.085 g, 0.17 mmol) as a white powder in a 34% yield.

Aufarbeitung

  1. additionis added
  2. additionis then added
  3. customThe reaction mixture is quenched with brine (15 mL)
  4. extractionextracted with Et2O (50 mL+2×25 mL)
  5. dry with materialAfter drying over MgSO4, evaporation under reduced pressure
  6. customthe crude compound is purified via flash chromatography on a 3×24 cm2 SiO2 column

Quellen und Nachweise

ORD-Eintrag
ord-4e6860f4b89f4c70b3dd8181fc9e21cc
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08053436B1

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