Acetyl chloride → 3-(1-Acetyl-piperidin-4-yl)-7-trifluoromethyl-benzo[b]thiophene-2-carboxylic acid methyl ester

HRID 456550Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 456550
[CH3:1][O:2][C:3]([C:5]1[S:9][C:8]2[C:10]([C:14]([F:17])([F:16])[F:15])=[CH:11][CH:12]=[CH:13][C:7]=2[C:6]=1[CH:18]1[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]1)=[O:4].C(N(CC)CC)C.C1C[O:34][CH2:33][CH2:32]1.C(Cl)(=O)C>C(OCC)(=O)C>[CH3:1][O:2][C:3]([C:5]1[S:9][C:8]2[C:10]([C:14]([F:16])([F:17])[F:15])=[CH:11][CH:12]=[CH:13][C:7]=2[C:6]=1[CH:18]1[CH2:23][CH2:22][N:21]([C:33](=[O:34])[CH3:32])[CH2:20][CH2:19]1)=[O:4]

Komponenten

6

Edukt 4

HCID 6367Acetyl chlorideHCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 588176523-Piperidin-4-yl-7-trifluoromethyl-benzo[b]thiophene-2-carboxylic acid methyl ester

Produkt 1

HCID 588175743-(1-Acetyl-piperidin-4-yl)-7-trifluoromethyl-benzo[b]thiophene-2-carboxylic acid methyl esterAusbeute 88 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a room temperature solution of 3-piperidin-4-yl-7-trifluoromethyl-benzo[b]thiophene-2-carboxylic acid methyl ester (4.37 g, 12.7 mmol), triethylamine (2.70 mL. 19.4 mmol), and anhydrous THF (80 mL) under nitrogen was added acetyl chloride (1.10 mL, 15.5 mmol) in one portion and the reaction stirred at room temperature overnight. The reaction was diluted with ethyl acetate (300 mL) and washed with water (150 mL) and brine (150 mL) successively. The organic layer was dried over magnesium sulfate, filtered, and the solvent removed. The residue was chromatographed on silica, eluting with 10% methanol/ethyl acetate, to afford 4.28 g (88%) of the desired product as a white solid, mp: 155.2° C.

Aufarbeitung

  1. washwashed with water (150 mL) and brine (150 mL) successively
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. filtrationfiltered
  4. customthe solvent removed
  5. customThe residue was chromatographed on silica
  6. washeluting with 10% methanol/ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-241fed9fba63418593d43959e35eb3cd
Quelldatensatz
uspto-grants-2007_03
Patentnummer
US07186724B2

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