Hydrochloric Acid → HCID 21503366, compound

HRID 1287984Notes

Reaction equation

HRID 1287984 reaction equation
O[CH2:2][CH2:3][CH:4]1[CH2:9][CH:8]2[CH2:10][CH2:11][N:5]1[CH2:6][CH2:7]2.Cl.S(Cl)([Cl:15])=O>C(Cl)(Cl)Cl>[Cl:15][CH2:2][CH2:3][CH:4]1[CH2:9][CH:8]2[CH2:10][CH2:11][N:5]1[CH2:6][CH2:7]2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 24386Thionyl ChlorideHCID 19917663HCID 19917663, compound

Product 1

HCID 21503366HCID 21503366, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of 10 g of 2-hydroxyethyl-quinuclidine in 80 ml of anhydrous chloroform was cooled to 0° C and treated with anhydrous gaseous hydrogen chloride. 50 ml of thionyl chloride were then added to the solution and the reaction mixture was heated to reflux for 3 hours. The excess thionyl chloride and the chloroform were removed by evaporation under reduced pressure on a water bath at 50° C. The residue was purified by washing with anhydrous ether. The ethereal suspension was filtered and the crystals obtained were dried under reduced pressure at room temperature. 12 g of 2-chloroethyl-quinuclidine, m.p. 202° C, were obtained.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureto reflux for 3 hours
  3. customThe excess thionyl chloride and the chloroform were removed by evaporation under reduced pressure on a water bath at 50° C
  4. customThe residue was purified
  5. washby washing with anhydrous ether
  6. filtrationThe ethereal suspension was filtered
  7. customthe crystals obtained
  8. customwere dried under reduced pressure at room temperature

Sources & evidence

ORD record
ord-4144aae8849d4983be80cc676ddf5e60
Source dataset
uspto-grants-1976_10
Patent number
US03987042

Reaction notes

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