Sodium hydride → 3-(1-Methylpyrrolidin-2-yl)pyridine

HRID 389170

Reaktionsgleichung

Reaktionsgleichung von HRID 389170
[N:1]1[CH:6]=[C:5]([C@H:7]2[CH2:12][CH2:11][CH2:10][N:8]2[CH3:9])[CH:4]=[CH:3][CH:2]=1.[H-].[Na+]>Cl>[CH3:9][N:8]1[CH:7]([C:5]2[CH:4]=[CH:3][CH:2]=[N:1][CH:6]=2)[CH2:12][CH2:11][CH2:10]1

Komponenten

4

Edukt 2

HCID 24758Sodium hydrideHCID 157672(R)-Nicotine

Produkt 1

HCID 9423-(1-Methylpyrrolidin-2-yl)pyridineAusbeute 66,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 313Hydrochloric AcidLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Sodium hydride (14.8 g, 0.616 mol of 60% dispersion in a mineral oil) was washed with toluene to remove the mineral oil and added to 100 ml of o-xylene. To this was added (R)-nicotine (10 g, 0.0617 mol). The reaction mixture was refluxed for 15 hrs, cooled to 0° C., the excess sodium hydride decomposed using dilute HCl (15%, 100 ml), the aqueous layer separated, the pH of the aqueous layer adjusted to >13 at 0° C. and extracted with dichloromethane. The solvent was then removed completely and the crude obtained was further purified by vacuum distillation at 0.1 mm Hg to get (R,S)-nicotine (6.68 g, 66.8% Y, 98.5% purity by GC, optical rotation: 0.8°)

Aufarbeitung

  1. washSodium hydride (14.8 g, 0.616 mol of 60% dispersion in a mineral oil) was washed with toluene
  2. customto remove the mineral oil
  3. additionadded to 100 ml of o-xylene
  4. temperatureThe reaction mixture was refluxed for 15 hrs
  5. customthe aqueous layer separated
  6. customadjusted to >13 at 0° C.
  7. extractionextracted with dichloromethane
  8. customThe solvent was then removed completely
  9. customthe crude obtained
  10. distillationwas further purified by vacuum distillation at 0.1 mm Hg

Quellen und Nachweise

ORD-Eintrag
ord-f92dc1a5e36848f287bd9a4baa5d43bb
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08378111B2

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