Carbon Dioxide → 3-Chloro-8-methyl-8-azabicyclo(3.2.1)octane

HRID 863829Notes

Reaction equation

HRID 863829 reaction equation
[CH3:1][N:2]1[C@@H:6]2[CH2:7][C@H:8](O)[CH2:9][C@H:3]1[CH2:4][CH2:5]2.S(Cl)([Cl:13])=O.[OH-].[Na+].C(=O)=O>C(Cl)Cl.C(Cl)(Cl)Cl>[Cl:13][CH:8]1[CH2:9][CH:3]2[N:2]([CH3:1])[CH:6]([CH2:5][CH2:4]2)[CH2:7]1

Participants

7

Reactant 4

HCID 280Carbon DioxideHCID 14798Sodium HydroxideHCID 24386Thionyl ChlorideHCID 178481185HCID 178481185, compound

Product 1

HCID 1375273-Chloro-8-methyl-8-azabicyclo(3.2.1)octane

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 95 g pseudotropine in 420 ml abs. CHCl3 are added dropwise at 0° 195 ml thionyl chloride within 20 minutes. The reaction mixture is refluxed for 4 hours, then left overnight at room temperature and then heated to 60°-65° for 3 hours. The mixture is then diluted with CH2Cl2 to a volume of ca. 100 to 150 ml and poured on ice-water. A 35% aqueous NaOH solution is added to a pH 11 and then dry ice to a pH 10. After extraction with CH2Cl2 and distillation of the extracts (second fraction~97°-98°) the title compound is obtained.

Workup

  1. temperatureThe reaction mixture is refluxed for 4 hours
  2. temperatureheated to 60°-65° for 3 hours
  3. additionpoured on ice-water
  4. extractionAfter extraction
  5. distillationwith CH2Cl2 and distillation of the extracts (second fraction~97°-98°) the title compound
  6. customis obtained

Sources & evidence

ORD record
ord-7d20ea0907b34d7e97ddae387d054fb0
Source dataset
uspto-grants-1996_10
Patent number
US05561149

Reaction notes

Loading…