Thionyl Chloride → 1-Benzyl-3-(chloromethyl)pyrrolidine

HRID 1450709

Reaktionsgleichung

Reaktionsgleichung von HRID 1450709
[CH2:1]([N:8]1[CH2:12][CH2:11][CH:10]([CH2:13]O)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(Cl)([Cl:17])=O>C(Cl)(Cl)Cl>[CH2:1]([N:8]1[CH2:12][CH2:11][CH:10]([CH2:13][Cl:17])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

4

Edukt 2

HCID 24386Thionyl ChlorideHCID 5176654(1-Benzylpyrrolidin-3-yl)methanol

Produkt 1

HCID 123645181-Benzyl-3-(chloromethyl)pyrrolidine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel2×

Versuchsvorschrift

To a refluxing solution of 15.3 g (0.08 mole) (3RS)-1-benzyl-3-hydroxymethyl pyrrolidine in 220 ml CHCl3 was slowly added a solution of 330 ml thionyl chloride in 60 ml CHCl3, and the reflux was continued for one hour. The mixture was evaporated and the residue was dissolved in water. The water layer was washed with ethyl acetate and then made alkaline with 0.2M NaOH-solution. The water layer was extracted three times with ethyl acetate and the combined organic layer was dried (Na2SO4), filtered and evaporated to give the product in a quantitative yield (16.8 g).

Aufarbeitung

  1. customThe mixture was evaporated
  2. dissolutionthe residue was dissolved in water
  3. washThe water layer was washed with ethyl acetate
  4. extractionThe water layer was extracted three times with ethyl acetate
  5. dry with materialthe combined organic layer was dried (Na2SO4)
  6. filtrationfiltered
  7. customevaporated
  8. customto give the product in a quantitative yield (16.8 g)

Quellen und Nachweise

ORD-Eintrag
ord-c53ac06b5f2e4b74aeb8fa2cf68952ec
Quelldatensatz
uspto-grants-1997_02
Patentnummer
US05602253

Verknüpfte Notizen

Wird geladen…