Thionyl Chloride → 3-Chloroquinolizidine

HRID 372233Notes

Reaction equation

HRID 372233 reaction equation
O[CH:2]1[CH2:11][N:10]2[CH:5]([CH2:6][CH2:7][CH2:8][CH2:9]2)[CH2:4][CH2:3]1.S(Cl)([Cl:14])=O>C1C=CC=CC=1>[Cl:14][CH:2]1[CH2:11][N:10]2[CH:5]([CH2:6][CH2:7][CH2:8][CH2:9]2)[CH2:4][CH2:3]1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 558277Octahydro-2H-quinolizin-3-ol

Product 1

HCID 203288343-Chloroquinolizidine

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of 14 g. (0.11 mole) of 3-hydroxyquinolizidine in 75 ml. of thionyl chloride and 50 ml. of benzene was refluxed for one hour. The solvent was completely evaporated, and the residue dissolved in chloroform. The solution was passed through an alumina column and evaporation of the chloroform gave crude 3-chloroquinolizidine. The crude material was chromatographed on an alumina column eluting with ether-petroleum ether, 1:19 to yield pure 3-chloroquinolizidine.

Workup

  1. customThe solvent was completely evaporated
  2. dissolutionthe residue dissolved in chloroform
  3. customThe solution was passed through an alumina column and evaporation of the chloroform
  4. customgave crude 3-chloroquinolizidine
  5. customThe crude material was chromatographed on an alumina column
  6. washeluting with ether-petroleum ether, 1:19

Sources & evidence

ORD record
ord-874dd641a47741bd9bc4880a83794e4c
Source dataset
uspto-grants-1978_05
Patent number
US04089961

Reaction notes

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