Potassium Carbonate → HCID 19007871, compound

HRID 1741643Notes

Reaction equation

HRID 1741643 reaction equation
ClC(OC=C)=O.[S:7]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[C:9]([CH:16]2[CH2:22][CH:21]3[N:23](C)[CH:18]([CH2:19][CH2:20]3)[CH2:17]2)=[N:8]1.C(=O)([O-])[O-].[K+].[K+]>ClCCCl>[S:7]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[C:9]([CH:16]2[CH2:22][CH:21]3[NH:23][CH:18]([CH2:19][CH2:20]3)[CH2:17]2)=[N:8]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 78808Vinyl chloroformateHCID 19007862HCID 19007862, compound

Product 1

HCID 19007871HCID 19007871, compoundYield 101%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

Vinyl chloroformate (4.4 g) was added dropwise to a solution of 3-(1,2-benzisothiazol-3-yl)-8-methyl-8-azabicyclo[3.2.1]octane (8.9 g) and potassium carbonate (4.76 g) in 250 ml of 1,2-dichloroethane. The resulting suspension was heated at reflux for 3 hours, and then the solution was cooled, and the solvent was removed in vacuo. The residue was suspended in isopropyl alcohol and acidified with HCl in isopropanol (to about a pH of 1 ), and the mixture was heated at reflux for 1 hour. The mixture was cooled, made basic, and then the product was extracted into dichloromethane. The combined organic layers were dried over MgSO4, filtered and concentrated to provide 8.5 g of 3-(1,2-benzisothiazol-3-yl)-8-azabicyclo[3.2.1]octane which was used subsequently without purification.

Workup

  1. temperatureThe resulting suspension was heated
  2. temperatureat reflux for 3 hours
  3. temperaturethe solution was cooled
  4. customthe solvent was removed in vacuo
  5. temperaturewas heated
  6. temperatureat reflux for 1 hour
  7. temperatureThe mixture was cooled
  8. extractionthe product was extracted into dichloromethane
  9. dry with materialThe combined organic layers were dried over MgSO4
  10. filtrationfiltered
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-7a0951c6940d4b23887a2a69cbcb9251
Source dataset
uspto-grants-1994_08
Patent number
US05334599

Reaction notes

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