Potassium Carbonate → HCID 19007872, compound

HRID 2254101Notes

Reaction equation

HRID 2254101 reaction equation
[Cl:1]C(OC=C)=O.[F:7][C:8]1[CH:25]=[CH:24][C:11]2[C:12]([CH:15]3[CH2:21][CH:20]4[N:22](C)[CH:17]([CH2:18][CH2:19]4)[CH2:16]3)=[N:13][O:14][C:10]=2[CH:9]=1.C(=O)([O-])[O-].[K+].[K+]>ClCCCl>[ClH:1].[F:7][C:8]1[CH:25]=[CH:24][C:11]2[C:12]([CH:15]3[CH2:16][CH:17]4[NH:22][CH:20]([CH2:19][CH2:18]4)[CH2:21]3)=[N:13][O:14][C:10]=2[CH:9]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 78808Vinyl chloroformateHCID 19007844HCID 19007844, compound

Product 1

HCID 19007872HCID 19007872, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

Vinyl chloroformate (2.9 g) was added dropwise to a solution of 3-(6-fluoro-1,2-benzisoxazol-3-yl)-8-methyl-8-azabicyclo[3.2.1]octane (5.6 g) and potassium carbonate (3.6 g) in 125 ml of 1,2-dichloroethane at 0° C. The resulting suspension was heated at reflux for 3 hours, the solution was cooled, and the solvent was removed in vacuo. The residue was suspended in 125 mL of ethanol and acidified with HCl in ethanol (to about a pH of 1), and the mixture was heated at reflux for 2 hours. The mixture was cooled, and 3.6 g of 3-(6-fluoro-1,2-benzisoxazol-3-yl)-8-azabicyclo[3.2.1]octane hydrochloride, m.p. 248°-250° C., crystallized out of solution.

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 2 hours
  7. temperatureThe mixture was cooled
  8. custom3.6 g of 3-(6-fluoro-1,2-benzisoxazol-3-yl)-8-azabicyclo[3.2.1]octane hydrochloride, m.p. 248°-250° C., crystallized out of solution

Sources & evidence

ORD record
ord-7820169e9a464c038a6dc7dc006fb127
Source dataset
uspto-grants-1993_08
Patent number
US05234931

Reaction notes

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