Sodium hydride → HCID 59833652, Verbindung

HRID 270044Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 270044
[H-].[Na+].[CH2:3]([N:10]1[CH2:15][CH2:14][C:13]([CH2:24][OH:25])([CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2F)[CH2:12][CH2:11]1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1>CCCCCCC.O1CCCC1>[CH2:3]([N:10]1[CH2:15][CH2:14][C:13]2([CH2:16][C:17]3[C:22](=[CH:21][CH:20]=[CH:19][CH:18]=3)[O:25][CH2:24]2)[CH2:12][CH2:11]1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Komponenten

5

Edukt 2

HCID 24758Sodium hydrideHCID 68961767[1-Benzyl-4-(2-fluorobenzyl)piperidin-4-yl)methanol

Produkt 1

HCID 59833652HCID 59833652, VerbindungAusbeute 89 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittel2×HCID 8900HeptaneLösungsmittel

Versuchsvorschrift

Sodium hydride (350 mg, 7.0 mmol, 50% disp in oil) was washed three times with heptane, under nitrogen atmosphere, and then dissolved in tetrahydrofuran (50 mL). A solution of [1-benzyl-4-(2-fluorobenzyl)piperidin-4-yl)methanol (1 g, 3.2 mmol) in tetrahydrofuran (30 mL) was added and the resulting mixture was refluxed for 3 hrs. The cooled solution was partitioned between water and ethyl acetate and the organic layer was dried over magnesium sulphate and concentrated. The crude product was purified on silica (dichloromethane/methanol) to give 0.83 g (89%) of the subtitle compound.

Aufarbeitung

  1. temperaturethe resulting mixture was refluxed for 3 hrs
  2. customThe cooled solution was partitioned between water and ethyl acetate
  3. dry with materialthe organic layer was dried over magnesium sulphate
  4. concentrationconcentrated
  5. customThe crude product was purified on silica (dichloromethane/methanol)

Quellen und Nachweise

ORD-Eintrag
ord-60bdd320967742c2853f7147e773af0d
Quelldatensatz
uspto-grants-2008_11
Patentnummer
US07449475B2

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