Reaction #961

ord-1537debbdfcd4c9fb2d97af472b6fc7c

Reaction equation

OCC1CCN(Cc2ccccc2)C1
(3RS)-1-benzyl-3-hydroxymethyl pyrrolidine
O=S(Cl)Cl
thionyl chloride
→
ClCC1CCN(Cc2ccccc2)C1
(3RS)-1-benzyl-3-chloromethyl pyrrolidine

Reactants

OCC1CCN(Cc2ccccc2)C1
(3RS)-1-benzyl-3-hydroxymethyl pyrrolidine
O=S(Cl)Cl
thionyl chloride

Reagents

None

Solvents

ClC(Cl)Cl
CHCl3
ClC(Cl)Cl
CHCl3

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    OtherThe mixture was evaporated
  2. 2
    workup.DISSOLUTIONthe residue was dissolved in water

Procedure

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.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US05723444uspto-grants-1998_03