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

HRID 1610807Notes

Reaction equation

HRID 1610807 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-hydroxymethylpyrrolidine 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-ed6dbfda700e48f385b89f859d909b15
Source dataset
uspto-grants-2006_01
Patent number
US06984627B1

Reaction notes

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