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

HRID 865

Reaction equation

HRID 865 reaction equation
[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

Participants

4

Reactant 2

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

Product 1

HCID 123645181-Benzyl-3-(chloromethyl)pyrrolidine

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

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.

Workup

  1. customThe mixture was evaporated
  2. dissolutionthe residue was dissolved in water

Sources & evidence

ORD record
ord-1537debbdfcd4c9fb2d97af472b6fc7c
Source dataset
uspto-grants-1998_03
Patent number
US05723444

Linked notes

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