Vinyl chloroformate → HCID 21915334, compound

HRID 1741637Notes

Reaction equation

HRID 1741637 reaction equation
[Cl:1]C(OC=C)=O.[O: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>ClCCCl>[ClH:1].[O: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

4

Reactant 2

HCID 78808Vinyl chloroformateHCID 15233767HCID 15233767, compound

Product 1

HCID 21915334HCID 21915334, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

Vinyl chloroformate (3.6 g) was added dropwise to a solution of 3-(1,2-benzisoxazol-3-yl)-8-methyl-8-azabicyclo[3.2.1]octane (6.0 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 isopropanol (to about a pH of 1), and the mixture was heated at reflux for 2 hours. The mixture was cooled, and 3.9 g of 3-( 1,2-benzisoxazol-3-yl)-8-azabicyclo[3.2.1 ]octane hydrochloride crystallized, m.p. 264°-268° C.

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. custom3.9 g of 3-( 1,2-benzisoxazol-3-yl)-8-azabicyclo[3.2.1 ]octane hydrochloride crystallized

Sources & evidence

ORD record
ord-284d0c0e8ab94de7bfca61f1f6776ff9
Source dataset
uspto-grants-1994_08
Patent number
US05334599

Reaction notes

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