Hydrochloric Acid → HCID 13959885, compound

HRID 2232086Notes

Reaction equation

HRID 2232086 reaction equation
[CH2:1]([N:8]1[CH2:12][CH:11](O)[CH:10]([CH2:14][N:15]=[N+:16]=[N-:17])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.S(Cl)([Cl:21])=O>C(Cl)(Cl)Cl>[CH2:1]([N:8]1[CH2:12][CH:11]([Cl:21])[CH:10]([CH2:14][N:15]=[N+:16]=[N-:17])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 24386Thionyl ChlorideHCID 14347788HCID 14347788, compound

Product 1

HCID 13959885HCID 13959885, compoundYield 40.3%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

1-Benzyl-4-hydroxy-3-azidomethylpyrrolidine (59.7 g) is added to chloroform (100 ml), and the mixture is saturated with dry hydrogen chloride gas. A solution of thionyl chloride (61.2 g) in chloroform (100 ml) is added dropwise to the mixture under reflux. After refluxing for 2 hours, the mixture is concentrated. To the residue is added ethanol and the excess thionyl chloride is removed, and then, the mixture is again concentrated. After neutralizing the concentrate with an aqueous sodium hydrogen carbonate, the mixture is extracted with dichloromethane. The dichloromethane layer is washed with water, dried and concentrated, and the resulting residue is then purified by silica gel column chromatography (solvent, ethyl acetate-n-hexane) to give 1-benzyl-3-azidomethyl-4-chloropyrrolidine (26.0 g) as an yellow oil.

Workup

  1. temperatureunder reflux
  2. temperatureAfter refluxing for 2 hours
  3. concentrationthe mixture is concentrated
  4. additionTo the residue is added ethanol
  5. customthe excess thionyl chloride is removed
  6. concentrationthe mixture is again concentrated
  7. concentrationconcentrate with an aqueous sodium hydrogen carbonate
  8. extractionthe mixture is extracted with dichloromethane
  9. washThe dichloromethane layer is washed with water
  10. customdried
  11. concentrationconcentrated
  12. customthe resulting residue is then purified by silica gel column chromatography (solvent, ethyl acetate-n-hexane)

Sources & evidence

ORD record
ord-07215b09304a409b95093bc8d529bcc4
Source dataset
uspto-grants-1988_11
Patent number
US04786649

Reaction notes

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