Réaction #1672672

Équation de réaction

(3RS)-1-benzyl-3-hydroxymethyl pyrrolidine

thionyl chloride

→

(3RS)-1-benzyl-3-chloromethyl pyrrolidine

Solvants

CHCl3

CHCl3

Conditions de réaction

Traitement

1. 1
   AutreThe mixture was evaporated
2. 2
   workup.DISSOLUTIONthe residue was dissolved in water
3. 3
   LavageThe water layer was washed with ethyl acetate
4. 4
   ExtractionThe water layer was extracted three times with ethyl acetate
5. 5
   Séchagethe combined organic layer was dried (Na2SO4)
6. 6
   Filtrationfiltered
7. 7
   Autreevaporated
8. 8
   Autreto give the product in a quantitative yield (16.8 g)

Mode opératoire

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 0.2 M 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).

Source