Acetyl chloride → 1-[3-(4-Bromophenyl)pyrrolidin-1-yl]ethanone

HRID 1054603Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1054603
C(N(CC)CC)C.Cl.[Br:9][C:10]1[CH:15]=[CH:14][C:13]([CH:16]2[CH2:20][CH2:19][NH:18][CH2:17]2)=[CH:12][CH:11]=1.[C:21](Cl)(=[O:23])[CH3:22]>C1COCC1.O>[Br:9][C:10]1[CH:11]=[CH:12][C:13]([CH:16]2[CH2:20][CH2:19][N:18]([C:21](=[O:23])[CH3:22])[CH2:17]2)=[CH:14][CH:15]=1

Komponenten

6

Edukt 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 534077083-(4-Bromophenyl)pyrrolidine hydrochloride

Produkt 1

HCID 842041851-[3-(4-Bromophenyl)pyrrolidin-1-yl]ethanoneAusbeute 117,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Triethylamine (192 mg, 1.9 mmol) was added to a suspension of 3-(4-bromophenyl)pyrrolidine hydrochloride (200 mg, 0.76 mmol) in anhydrous THF (5 mL). The mixture was stirred at room temperature for 5 minutes and then treated with acetyl chloride (66 mg, 0.84 mmol). The reaction mixture was stirred for 20 hours at room temperature. The reaction mixture was diluted with water and extracted with EtOAc (2×20 mL). The combined organic layers were washed with brine, dried over Na2SO4 and concentrated in vacuo to give 1-[3-(4-bromophenyl)pyrrolidin-1-yl]ethanone (0.24 g, quantitative yield) as an oil which was used directly in the next step. MS (ES+) 267.9 (M+H)+.

Aufarbeitung

  1. stirringThe reaction mixture was stirred for 20 hours at room temperature
  2. extractionextracted with EtOAc (2×20 mL)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-8eb867e16a9d414592188ed83c7b47b6
Quelldatensatz
uspto-grants-2016_07
Patentnummer
US09394285B2

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