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Sodium Iodide → (R)-2-Hydroxymethyl-1-[3-(4-methoxyphenyl)propyl]piperidine

HRID 1859428
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1859428
[OH:1][CH2:2][C@H:3]1[CH2:8][CH2:7][CH2:6][CH2:5][NH:4]1.S(O[CH2:14][CH2:15][CH2:16][C:17]1[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=1)(=O)(=O)C.C(=O)([O-])[O-].[Na+].[Na+].[I-].[Na+]>C(#N)C>[OH:1][CH2:2][C@H:3]1[CH2:8][CH2:7][CH2:6][CH2:5][N:4]1[CH2:14][CH2:15][CH2:16][C:17]1[CH:18]=[CH:19][C:20]([O:23][CH3:24])=[CH:21][CH:22]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 5238Sodium IodideHCID 10340Sodium CarbonateHCID 6950192(2R)-piperidin-2-ylmethanolHCID 116659383-(4-Methoxyphenyl)propyl methanesulfonate

Produkt 1

HCID 57440105(R)-2-Hydroxymethyl-1-[3-(4-methoxyphenyl)propyl]piperidine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342
Acetonitrile
Lösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

(R)-2-hydroxymethylpiperidine (288 mg, 2.50 mmol), 3-(4-methoxyphenyl)propyl mesylate (915 mg, 3.75 mmol), sodium carbonate (398 mg, 3.75 mmol) and sodium iodide (30 mg, 0.20 mmol) were added to acetonitrile (25 ml), and they were heated under reflux at 90° C. for 6 hours. The solvent was evaporated under reduced pressure. The residue was distributed in ethyl acetate and saturated aqueous sodium hydrogencarbonate solution. The organic layer was washed with water and dried over magnesium sulfate. Then the solvent was evaporated under reduced pressure. The obtained residue was subjected to silica gel column chromatography. The product was eluted with dichloromethane as the eluent and then with dichloromethane and methanol (20:1). The appropriate fractions were combined, and the solvent was evaporated under reduced pressure to obtain (R)-2-hydroxymethyl-1-[3-(4-methoxy-phenyl) propyl]piperidine in the form of a light yellow oil (422 mg, 64%).

Aufarbeitung

  1. temperaturewere heated
  2. customThe solvent was evaporated under reduced pressure
  3. washThe organic layer was washed with water
  4. dry with materialdried over magnesium sulfate
  5. customThen the solvent was evaporated under reduced pressure
  6. washThe product was eluted with dichloromethane as the eluent
  7. customthe solvent was evaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-405fd2795f4448eab5b165fef8003740
Quelldatensatz
uspto-grants-2003_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06528504B2

Notizen zur Reaktion

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