Tetrahydrofuran → 4-(1H-Imidazol-1-yl)phenyl-4-methyl-1-piperidine ethanol

HRID 232335

Reaktionsgleichung

Reaktionsgleichung von HRID 232335
Br[CH2:2][CH:3]([C:5]1[CH:10]=[CH:9][C:8]([N:11]2[CH:15]=[CH:14][N:13]=[CH:12]2)=[CH:7][CH:6]=1)O.[CH3:16][CH:17]1[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1.[O:23]1CCCC1>>[N:11]1([C:8]2[CH:9]=[CH:10][C:5]([CH:3]3[CH2:2][CH:17]([CH3:16])[CH2:18][CH2:19][N:20]3[CH2:21][CH2:22][OH:23])=[CH:6][CH:7]=2)[CH:15]=[CH:14][N:13]=[CH:12]1

Komponenten

4

Edukt 3

HCID 8028TetrahydrofuranHCID 693814-MethylpiperidineHCID 20031362alpha-(Bromomethyl)-4-(1H-imidazol-1-yl)benzenemethanol

Produkt 1

HCID 178455204-(1H-Imidazol-1-yl)phenyl-4-methyl-1-piperidine ethanol

Versuchsvorschrift

Add α-(bromomethyl)-4-(1H-imidazol-1-yl)benzenemethanol (8.88 g, 33.24 mmol) to a room temperature solution of 4-methylpiperidine (11.8 mL, 99.73 mmol) in tetrahydrofuran (90mL). Stir the resultant mixture for 2.5 days and concentrate in vacuo. Chromatograph the residue on alumina (neutral, activity III, 100 g) using first methylene chloride than 2% methanol in methylene chloride as eluent. Collect the product fraction and concentrate in vacuo to give a solid. Recrystallize the solid from petroleum ether/ethyl acetate (ca. 4+1). Drying at 50° C. for 2 hr at p=1.0 mm affords the title compound.

Aufarbeitung

  1. concentrationconcentrate in vacuo
  2. customCollect the product fraction
  3. concentrationconcentrate in vacuo
  4. customto give a solid
  5. customRecrystallize the solid from petroleum ether/ethyl acetate (ca. 4+1)
  6. customDrying at 50° C. for 2 hr at p=1.0 mm

Quellen und Nachweise

ORD-Eintrag
ord-5c272afe37204cc6941c112a84e35e56
Quelldatensatz
uspto-grants-1989_07
Patentnummer
US04851526

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