Diisopropylethylamine → 2-(4-Fluorophenyl)-2-[3-[4-(6-fluorobenzo[b]thiophen-3-yl)piperidin-1-yl]propyl]-1,3-dioxolane

HRID 393180

Reaktionsgleichung

Reaktionsgleichung von HRID 393180
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([CH2:13][CH2:14][CH2:15]Cl)[O:12][CH2:11][CH2:10][O:9]2)=[CH:4][CH:3]=1.Cl.[F:18][C:19]1[CH:20]=[CH:21][C:22]2[C:26]([CH:27]3[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]3)=[CH:25][S:24][C:23]=2[CH:33]=1.C(N(C(C)C)CC)(C)C>CO>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([CH2:13][CH2:14][CH2:15][N:30]3[CH2:31][CH2:32][CH:27]([C:26]4[C:22]5[CH:21]=[CH:20][C:19]([F:18])=[CH:33][C:23]=5[S:24][CH:25]=4)[CH2:28][CH2:29]3)[O:12][CH2:11][CH2:10][O:9]2)=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 81531DiisopropylethylamineHCID 27237782-(3-Chloropropyl)-2-(4-fluorophenyl)-1,3-dioxolaneHCID 22649334HCID 22649334, Verbindung

Produkt 1

HCID 226493442-(4-Fluorophenyl)-2-[3-[4-(6-fluorobenzo[b]thiophen-3-yl)piperidin-1-yl]propyl]-1,3-dioxolaneAusbeute 29 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

A mixture of 1.5 g of 2-(4-fluorophenyl)-2-(3-chloropropyl)-1,3-dioxolane, 1.5 g of 4-(6-fluorobenzo[b]thiophen-3-yl)piperidine hydrochloride, 3.3 ml of diisopropylethylamine and 2.5 ml of methanol was stirred with heating under reflux for 25 hours. The reaction mixture was separated with chloroform and a saturated aqueous sodium hydrogencarbonate solution, and the aqueous layer was extracted with chloroform. The combined organic layer was washed with water and a saturated aqueous sodium chloride solution and then dried over magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by a flush chromatography (silica gel: Merckkieselgel 60 230- to 400-mesh, eluent: hexane-ethyl acetate=1:2) to obtain 0.71 g of 2-(4-fluorophenyl)-2-[3-[4-(6-fluorobenzo[b]thiophen-3-yl)piperidin-1-yl]propyl]-1,3-dioxolane.

Aufarbeitung

  1. temperaturewith heating
  2. temperatureunder reflux for 25 hours
  3. customThe reaction mixture was separated with chloroform
  4. extractiona saturated aqueous sodium hydrogencarbonate solution, and the aqueous layer was extracted with chloroform
  5. washThe combined organic layer was washed with water
  6. dry with materiala saturated aqueous sodium chloride solution and then dried over magnesium sulfate
  7. distillationThe solvent was distilled off under reduced pressure
  8. customthe residue was purified by a flush chromatography (silica gel: Merckkieselgel 60 230- to 400-mesh, eluent: hexane-ethyl acetate=1:2)

Quellen und Nachweise

ORD-Eintrag
ord-1e4df0f98c68444fb1f8885068f3f2ca
Quelldatensatz
uspto-grants-2004_10
Patentnummer
US06806275B2

Verknüpfte Notizen

Wird geladen…