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

HRID 1585490Notes

Reaction equation

HRID 1585490 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. 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).

Workup

  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)

Sources & evidence

ORD record
ord-72eabc5cac6a4b7e8288cb56f067245e
Source dataset
uspto-grants-1999_08
Patent number
US05939392

Reaction notes

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