Hydrochloric Acid → 2-(3-Bromo-4-(4-(thiophen-2-ylsulfonyl)piperazin-1-yl)phenyl)-1,1,1-trifluoro-2-propanol

HRID 1972446Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1972446
[Br:1][C:2]1[CH:7]=[C:6]([C:8]([OH:14])([CH3:13])[C:9]([F:12])([F:11])[F:10])[CH:5]=[CH:4][C:3]=1[N:15]1[CH2:20][CH2:19][N:18](C(OC(C)(C)C)=O)[CH2:17][CH2:16]1.Cl.O1CCOCC1.C(N(CC)CC)C.[S:42]1[CH:46]=[CH:45][CH:44]=[C:43]1[S:47](Cl)(=[O:49])=[O:48]>CCOC(C)=O>[Br:1][C:2]1[CH:7]=[C:6]([C:8]([OH:14])([CH3:13])[C:9]([F:10])([F:12])[F:11])[CH:5]=[CH:4][C:3]=1[N:15]1[CH2:16][CH2:17][N:18]([S:47]([C:43]2[S:42][CH:46]=[CH:45][CH:44]=2)(=[O:49])=[O:48])[CH2:19][CH2:20]1

Komponenten

7

Edukt 5

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 312751,4-DioxaneHCID 855182-Thiophenesulfonyl chlorideHCID 66582356Tert-butyl 4-(2-bromo-4-(2,2,2-trifluoro-1-hydroxy-1-methylethyl)phenyl)-1-piperazinecarboxylate

Produkt 1

HCID 665829132-(3-Bromo-4-(4-(thiophen-2-ylsulfonyl)piperazin-1-yl)phenyl)-1,1,1-trifluoro-2-propanolAusbeute 67,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A 250 mL round-bottomed flask was charged with tert-butyl 4-(2-bromo-4-(2,2,2-trifluoro-1-hydroxy-1-methylethyl)phenyl)-1-piperazinecarboxylate (3.70 g, 8.16 mmol), 25 mL of EtOAc, and 8 mL of 4M HCl in dioxane (32 mmol). After heating at reflux for 30 min, the mixture was cooled and concentrated. The resulting viscous oil was dissolved in 30 mL of CH2Cl2 and triethylamine (3.98 mL, 28.6 mmol). At 0° C., 2-thiophenesulfonyl chloride (1.49 g, 8.16 mmol, Sigma-Aldrich, St. Louis, Mo.) was added at 0° C. After 15 min, the mixture was concentrated then re-dissolved in 5 mL of CH2Cl2, filtered, and purified via column chromatography (120 g of silica, 0 to 50% EtOAc in hexanes) to give 2-(3-bromo-4-(4-(thiophen-2-ylsulfonyl)piperazin-1-yl)phenyl)-1,1,1-trifluoro-2-propanol (2.75 g) as a white solid.

Aufarbeitung

  1. temperatureAfter heating
  2. temperatureat reflux for 30 min
  3. temperaturethe mixture was cooled
  4. concentrationconcentrated
  5. dissolutionThe resulting viscous oil was dissolved in 30 mL of CH2Cl2
  6. concentrationthe mixture was concentrated
  7. dissolutionthen re-dissolved in 5 mL of CH2Cl2
  8. filtrationfiltered
  9. custompurified via column chromatography (120 g of silica, 0 to 50% EtOAc in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-9550fbd33772405bbd691f43f9f7b2a4
Quelldatensatz
uspto-grants-2013_04
Patentnummer
US08431563B2

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